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With the critical role of 3,3′-diaryl substituents of 1 in mind, we examined the effect of 4,4′- and 6,6′-substituents of one binaphthyl subunit

Recent development and application of chiral phase-transfer catalysts.

CHEMICAL REVIEWS, no. 12.0 (2007): 5656-5682

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Abstract

Takuya Hashimoto was born in Osaka, Japan. He received his Ph.D. degree (2006) from Kyoto University under the direction of Professor Keiji Maruoka. After spending one year as a postdoctoral researcher, he was appointed as an assistant professor at Kyoto University in 2007. His research interests include the design of chiral acid and base...More

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Introduction
  • Takuya Hashimoto was born in Osaka, Japan. He received his Ph.D. degree (2006) from Kyoto University under the direction of Professor Keiji Maruoka.
  • In the reaction with the simple alkyl halides such as ethyl iodide, use of aqueous cesium hydroxide (CsOH) as a basic phase at lower reaction temperature (-15 °C) is recommended.
  • Since both enantiomers of the catalyst of type 1 can be readily assembled in exactly the same manner starting from either (S)- or (R)-1,1′-bi-2-naphthol, a wide.
Highlights
  • Takuya Hashimoto was born in Osaka, Japan
  • The salient feature of 1e as a chiral phase-transfer catalyst is its ability to catalyze the asymmetric alkylation of glycine methyl and ethyl ester derivatives 4 and 5 with excellent enantioselectivities
  • With the critical role of 3,3′-diaryl substituents of 1 in mind, we examined the effect of 4,4′- and 6,6′-substituents of one binaphthyl subunit
  • To fully induce the potential catalytic activity of N-spiro chiral ammonium salt such as 1d, we have developed binary phase-transfer catalysis using an appropriate achiral cocatalyst
  • The development of various types of chiral phase-transfer catalysts largely relies on the molecular design of both natural product-derived and purely synthetic chiral quaternary ammonium salts, which often delivers higher reactivity and stereoselectivity and new synthetic opportunities, expanding the applicability of asymmetric phase-transfer catalysis in modern organic synthesis
  • Continuous efforts should be made toward the understanding of the relationship between the structure of the catalyst and its activity and stereocontrolling ability
Results
  • Sonication of the reaction mixture of 2, methyl iodide, and (S,S)-1c (1 mol %) in toluene-50% KOH aqueous solution at 0 °C for 1 h gave rise to the corresponding alkylation product in 63% yield with 88% ee, demonstrating that the reaction was sped up markedly, and the chemical yield and enantioselectivity were comparable with those of the reaction with simple stirring (0 °C for 8 h; 64%, 90% ee) (Scheme 4).[10].
  • Cahard and co-workers introduced cinchonidine-derived quaternary ammonium salt grafted to a poly(ethylene glycol) matrix 48c as an efficient homogeneous catalyst for the asymmetric alkylation of 2, and up to 81% ee was attained in the benzylation under standard liquid-liquid phase-transfer conditions.[49]
Conclusion
  • The development of various types of chiral phase-transfer catalysts largely relies on the molecular design of both natural product-derived and purely synthetic chiral quaternary ammonium salts, which often delivers higher reactivity and stereoselectivity and new synthetic opportunities, expanding the applicability of asymmetric phase-transfer catalysis in modern organic synthesis.
  • Continuous efforts should be made toward the understanding of the relationship between the structure of the catalyst and its activity and stereocontrolling ability
  • Systematic accumulation of such knowledge would allow them to conduct even more rational catalyst design for pursuing selective chemical synthesis in a manner of reliable and practical elegance, thereby allowing them to establish genuinely sustainable chemical processes within the context of the forthcoming paradigm shift in worldwide production of highly valuable substances in this century
Funding
  • Indeed, sonication of the reaction mixture of 2, methyl iodide, and (S,S)-1c (1 mol %) in toluene-50% KOH aqueous solution at 0 °C for 1 h gave rise to the corresponding alkylation product in 63% yield with 88% ee (enantiomeric excess), demonstrating that the reaction was sped up markedly, and the chemical yield and enantioselectivity were comparable with those of the reaction with simple stirring (0 °C for 8 h; 64%, 90% ee) (Scheme 4).[10]
  • Cahard and co-workers also introduced cinchonidine-derived quaternary ammonium salt grafted to a poly(ethylene glycol) matrix 48c as an efficient homogeneous catalyst for the asymmetric alkylation of 2, and up to 81% ee was attained in the benzylation under standard liquid-liquid phase-transfer conditions.[49]
Reference
  • (1) (a) Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis, 3rd ed.; VCH: Weinheim, Germany, 1993. (b) Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-Transfer Catalysis; Chapman & Hall: New York, 1994. (c) Sasson, Y., Neumann, R., Eds. Handbook of PhaseTransfer Catalysis; Blackie Academic & Professional: London, 1997. (d) Halpern, M. E., Ed. Phase-Transfer Catalysis; ACS Symposium Series 659; American Chemical Society: Washington, DC, 1997.
    Google ScholarLocate open access versionFindings
  • (2) (a) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y., Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14. (b) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583. (c) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, Germany, 2000; p 123. (d) O’Donnell, M. J. In Catalytic Asymmetric Syntheses, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10. (e) O’Donnell, M. J. Aldrichim. Acta 2001, 34, 3. (f) Maruoka, K.; Ooi, T. Chem. ReV. 2003, 103, 3013. (g) O’Donnell, M. J. Acc. Chem. Res. 2004, 37, 506. (h) Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518. (i) Vachon, J.; Lacour, J. Chimia 2006, 60, 266.
    Google ScholarLocate open access versionFindings
  • (3) (a) Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446. (b) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745.
    Google ScholarLocate open access versionFindings
  • (4) (a) O’Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353. (b) Lipkowitz, K. B.; Cavanaugh, M. W.; Baker, B.; O’Donnell, M. J. J. Org. Chem. 1991, 56, 5181. (c) Esikova, I. A.; Nahreini, T. S.; O’Donnell, M. J. In Phase-Transfer Catalysis; ACS Symposium Series 659; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997; Chapter 7. (d) O’Donnell, M. J.; Esikova, I. A.; Shullenberger, D. F.; Wu, S. In Phase-Transfer Catalysis; ACS Symposium Series 659; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997; Chapter 10.
    Google ScholarLocate open access versionFindings
  • (5) (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 859(b) Lygo, B.; Crosby, J.; Lowdon, T. R.; Wainwright, P. G. Tetrahedron 2001, 57, 2391. (c) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403. (d) Lygo, B.; Andrews, B. I.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 2002, 43, 8015.
    Google ScholarLocate open access versionFindings
  • (6) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.
    Google ScholarLocate open access versionFindings
  • (7) (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Maruoka, K. J. Fluorine Chem. 2001, 112, 95. (c) Ooi, T.; Uematsu, Y.; Maruoka, K. AdV. Synth. Catal. 2002, 344, 288. (d) Ooi, T.; Uematsu, Y.; Maruoka, K. J. Org. Chem. 2003, 68, 4576. (e) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
    Google ScholarLocate open access versionFindings
  • (8) Ooi, T.; Uematsu, Y.; Maruoka, K. Tetrahedron Lett. 2004, 45, 1675.
    Google ScholarFindings
  • (9) (a) Hashimoto, T.; Maruoka, K. Tetrahedron Lett. 2003, 44, 3313. (b) Hashimoto, T.; Tanaka, Y.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1599.
    Google ScholarLocate open access versionFindings
  • (10) Ooi, T.; Tayama, E.; Doda, K.; Takeuchi, M.; Maruoka, K. Synlett 2000, 1500.
    Google ScholarLocate open access versionFindings
  • (11) Shirakawa, S.; Yamamoto, K.; Kitamura, M.; Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2005, 44, 625.
    Google ScholarLocate open access versionFindings
  • (12) (a) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. (b) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Tetrahedron 2006, 62, 11425.
    Google ScholarLocate open access versionFindings
  • (13) Kano, T.; Konishi, S.; Shirakawa, S.; Maruoka, K. Tetrahedron: Asymmetry 2004, 15, 1243.
    Google ScholarLocate open access versionFindings
  • (14) Kitamura, M.; Shirakawa, S.; Maruoka, K. Angew. Chem., Int. Ed. 2005, 44, 1549.
    Google ScholarLocate open access versionFindings
  • (15) Ooi, T.; Kubota, Y.; Maruoka, K. Synlett 2003, 1931.
    Google ScholarLocate open access versionFindings
  • (16) Han, Z.; Yamaguchi, Y.; Kitamura, M.; Maruoka, K. Tetrahedron
    Google ScholarFindings
  • Lett. 2005, 46, 8555.
    Google ScholarFindings
  • (17) Jew, S.-s.; Yoo, M.-S.; Jeong, B.-S.; Park, I. Y.; Park, H.-g. Org.
    Google ScholarFindings
  • Lett. 2002, 4, 4245.
    Google ScholarFindings
  • (18) Yoo, M.-S.; Jeong, B.-S.; Lee, J.-H.; Park, H.-g.; Jew, S.-s. Org.
    Google ScholarLocate open access versionFindings
  • Lett. 2005, 7, 1129.
    Google ScholarFindings
  • (19) Elango, S.; Venugopal, M.; Suresh, P. S.; Eni Tetrahedron 2005, 61, 1443.
    Google ScholarFindings
  • (20) Kumar, S.; Ramachandran, U. Tetrahedron 2005, 61, 7022. (21) (a) Guillena, G.; Kreiter, R.; van de Coevering, R.; Klein Gebbink, R. J. M.; van Koten, G.; Mazon, P.; Chinchilla, R.; Najera, C. Tetrahedron: Asymmetry 2003, 14, 3705. (b) Mazon, P.; Chinchilla, R.; Najera, C.; Guillena, G.; Kreiter, R.; Klein Gebbink, R. J. M.; van Koten, G. Tetrahedron: Asymmetry 2002, 13, 2181.
    Google ScholarLocate open access versionFindings
  • (22) Andrus, M. B.; Ye, Z.; Zhang, J. Tetrahedron Lett. 2005, 46, 3839. (23) (a) Jew, S.-s.; Jeong, B.-S.; Yoo, M.-S.; Huh, H.; Park, H.-g. Chem. Commun. 2001, 1244. (b) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, B.-s.; Kim, M. G.; Jew, S.-s. Tetrahedron Lett. 2003, 44, 3497.
    Google ScholarLocate open access versionFindings
  • (24) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Park, M.-k.; Huh, H.; Jew, S.-s. Tetrahedron Lett. 2001, 42, 4645.
    Google ScholarLocate open access versionFindings
  • (25) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-k.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-s. Angew. Chem., Int. Ed. 2002, 41, 3036. (26) (a) Chinchilla, R.; Mazon, P.; Najera, C.; Ortega, F. J. Tetrahedron: Asymmetry 2004, 15, 2603. (b) Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2002, 13, 927. (27) (a) Siva, A.; Murugan, E. Synthesis 2005, 2927. (b) Siva, A.; Murugan, E. J. Mol. Catal. A: Chem. 2005, 241, 111. (c) Siva, A.; Murugan, E. J. Mol. Catal. A: Chem. 2006, 248, 1. (28) (a) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539. (b) Ohshima, T.; Shibuguchi, T.; Fukuta, Y.; Shibasaki, M. Tetrahedron 2004, 60, 7743.
    Google ScholarLocate open access versionFindings
  • (29) Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832. (30) (a) Kowtoniuk, W. E.; MacFarland, D. K.; Grover, G. N. Tetrahedron Lett. 2005, 46, 5703. See also: (b) Rueffer, M. E.; Fort, L. K.; MacFarland, D. K. Tetrahedron: Asymmetry 2004, 15, 3297. See also ref 35.
    Google ScholarFindings
  • (31) Sasai, H. Jpn. Kokai Tokkyo Koho 2003, JP2003335780. (32) (a) Lygo, B.; Allbutt, B.; James, S. R. Tetrahedron Lett. 2003, 44, 5629. (b) Lygo, B.; Allbutt, B. Synlett 2004, 326.
    Google ScholarLocate open access versionFindings
  • (33) Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073. (34) (a) Kumar, S.; Ramachandran, U. Tetrahedron 2005, 61, 4141. (b) Kumar, S.; Sobhia, M. E.; Ramachandran, U. Tetrahedron: Asymmetry 2005, 16, 2599.
    Google ScholarLocate open access versionFindings
  • (35) Grover, G. N.; Kowtoniuk, W. E.; MacFarland, D. K. Tetrahedron Lett. 2006, 47, 57.
    Google ScholarFindings
  • (36) Deleted in proof.
    Google ScholarFindings
  • (37) Chinchilla, R.; Najera, C.; Ortega, F. J. Tetrahedron: Asymmetry 2006, 17, 3423.
    Google ScholarLocate open access versionFindings
  • (38) Mase, N.; Ohno, T.; Morimoto, H.; Nitta, F.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2005, 46, 3213.
    Google ScholarFindings
  • (39) Li, L.; Zhang, Z.; Zhu, X.; Popa, A. Wang, S. Synlett 2005, 1869.
    Google ScholarLocate open access versionFindings
  • (40) Ooi, T.; Arimura, Y.; Hiraiwa, Y.; Yuan, L. M.; Kano, T.; Inoue, T.; Matsumoto, J.; Maruoka, K. Tetrahedron: Asymmetry 2006, 17, 603.
    Google ScholarLocate open access versionFindings
  • (41) Hyett, D. J.; Didone, M.; Milcent, T. J. A.; Broxterman, Q. B.; Kaptein, B. Tetrahedron Lett. 2006, 47, 7771.
    Google ScholarFindings
  • (42) Kumar, S.; Ramachandran, U. Tetrahedron: Asymmetry 2003, 14, 2539.
    Google ScholarFindings
  • (43) Ooi, T.; Sakai, D.; Takeuchi, M.; Tayama, E.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 5868.
    Google ScholarLocate open access versionFindings
  • (44) Ooi, T.; Takeuchi, M.; Kato, D.; Uematsu, Y.; Tayama, E.; Sakai, D.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 5073.
    Google ScholarLocate open access versionFindings
  • (45) Lepine, R.; Carbonnelle, A.-C.; Zhu, J. Synlett 2003, 1455.
    Google ScholarLocate open access versionFindings
  • (46) Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331. (47) (a) Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry
    Google ScholarFindings
  • 2000, 11, 3277. (b) Chinchilla, R.; Mazon, P.; Najera, C. AdV. Synth. Catal. 2004, 346, 1186.
    Google ScholarLocate open access versionFindings
  • (48) Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
    Google ScholarLocate open access versionFindings
  • (49) Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671.
    Google ScholarLocate open access versionFindings
  • (50) Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J.-C.; Cahard, D. Synthesis 2001, 1742.
    Google ScholarLocate open access versionFindings
  • (51) Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461. (52) (a) Yu, H.; Koshima, H. Tetrahedron Lett. 2003, 44, 9209. (b) Yu, H.; Takigawa, S.; Koshima, H. Tetrahedron 2004, 60, 8405.
    Google ScholarLocate open access versionFindings
  • (53) Shirakawa, S.; Tanaka, Y.; Maruoka, K. Org. Lett. 2004, 6, 1429.
    Google ScholarFindings
  • (54) Park, H.-g.; Kim, M.-J.; Park, M.-K.; Jung, H.-J.; Lee, J.; Choi, S.h.; Lee, Y.-J.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Ku, J.-M.; Jew, S.-s. J. Org. Chem. 2005, 70, 1904.
    Google ScholarLocate open access versionFindings
  • (55) Nitz, M.; Mezo, A. R.; Ali, M. H.; Imperiali, B. Chem. Commun. 2002, 1912.
    Google ScholarLocate open access versionFindings
  • (56) Lygo, B.; Andrews, B. I. Tetrahedron Lett. 2003, 44, 4499.
    Google ScholarFindings
  • (57) Lygo, B.; Andrews, B. I.; Slack, D. Tetrahedron Lett. 2003, 44, 9039.
    Google ScholarFindings
  • (58) Lygo, B.; Humphreys, L. D. Tetrahedron Lett. 2002, 43, 6677.
    Google ScholarFindings
  • (59) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339.
    Google ScholarFindings
  • (60) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716.
    Google ScholarLocate open access versionFindings
  • (61) Lemaire, C.; Gillet, S.; Guillouet, S.; Plenevaux, A.; Aerts, J.; Luxen, A. Eur. J. Org. Chem. 2004, 2899.
    Google ScholarLocate open access versionFindings
  • (62) Kumar, S.; Ramachandran, U. Tetrahedron Lett. 2005, 46, 19.
    Google ScholarFindings
  • (63) Castle, S. L.; Srikanth, G. S. C. Org. Lett. 2003, 5, 3611.
    Google ScholarFindings
  • (64) Boeckman, R. K., Jr.; Clark, T. J.; Shook, B. C. Org. Lett. 2002, 4, 2109.
    Google ScholarFindings
  • (65) Kim, S.; Lee, J.; Lee, T.; Park, H.-g.; Kim, D. Org. Lett. 2003, 5, 2703. (66) (a) Ohshima, T.; Gnanadesikan, V.; Shibuguchi, T.; Fukuta, Y.; Nemoto, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 11206. (b) Fukuta, Y.; Ohshima, T.; Gnanadesikan, V.; Shibuguchi, T.; Nemoto, T.; Kisugi, T.; Okino, T.; Shibasaki, M. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 5433.
    Google ScholarLocate open access versionFindings
  • (67) Lee, J.-H.; Jeong, B.-S.; Ku, J.-M.; Jew, S.-s.; Park, H.-g. J. Org. Chem. 2006, 71, 6690.
    Google ScholarLocate open access versionFindings
  • (68) Patterson, D. E.; Xie, S.; Jones, L. A.; Osterhout, M. H.; Henry, C. G.; Roper, T. D. Org. Process Res. DeV. 2007, 11, 624. (69) (a) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3329. (b) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. J. Org. Chem. 2002, 67, 7418.
    Google ScholarLocate open access versionFindings
  • (70) Ramachandran, P. V.; Madhi, S.; Bland-Berry, L.; Ram Reddy, M. V.; O’Donnell, M. J. J. Am. Chem. Soc. 2005, 127, 13450. (71) (a) Vogt, H.; Brase, S. Org. Biomol. Chem. 2007, 5, 406. (b) Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127. (c) Cativiela, C.; Dıaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517. (d) Schollkopf, U. Top. Curr. Chem. 1983, 109, 65.
    Google ScholarLocate open access versionFindings
  • (72) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228.
    Google ScholarLocate open access versionFindings
  • (73) Maeda, K.; Miller, R. A.; Szumigala, R. H., Jr.; Shafiee, A.; Karady, S.; Armstrong, J. D., III Tetrahedron Lett. 2005, 46, 1545.
    Google ScholarFindings
  • (74) Jew, S.-s.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Lee, Y.-J.; Park, B.-s.; Kim, M. G.; Park, H.-g. J. Org. Chem. 2003, 68, 4514.
    Google ScholarLocate open access versionFindings
  • (75) Jew, S.-s.; Lee, Y.-J.; Lee, J.; Kang, M. J.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Kim, M.-J.; Choi, S.-h.; Ku, J.-M.; Park, H.-g. Angew. Chem., Int. Ed. 2004, 43, 2382.
    Google ScholarLocate open access versionFindings
  • (76) Lee, Y.-J.; Lee, J.; Kim, M.-J.; Kim, T.-S.; Park, H.-g.; Jew, S.-s. Org. Lett. 2005, 7, 1557.
    Google ScholarLocate open access versionFindings
  • (77) Kim, T.-S.; Lee, Y.-J.; Jeong, B.-S.; Park, H.-g.; Jew, S.-s. J. Org. Chem. 2006, 71, 8276.
    Google ScholarLocate open access versionFindings
  • (78) For a comprehensive review on the use of peptide enolates, see: Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods; Ernst, B., Leumann, C., Eds.; VCH: Weinheim, Germany, 1995; Vol. 7, p 1. (79) (a) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 579. (b) Maruoka, K.; Tayama, E.; Ooi, T. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 5824.
    Google ScholarLocate open access versionFindings
  • (80) Dehmlow, E. V.; Duttmann, S.; Neumann, B.; Stammler, H.-G. Eur. J. Org. Chem. 2002, 2087.
    Google ScholarLocate open access versionFindings
  • (81) (a) Ooi, T.; Miki, T.; Taniguchi, M.; Shiraishi, M.; Takeuchi, M.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 3796. (b) Ooi, T.; Miki, T.; Fukumoto, K.; Maruoka, K. AdV. Synth. Catal. 2006, 348, 1539.
    Google ScholarLocate open access versionFindings
  • (82) Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897.
    Google ScholarLocate open access versionFindings
  • (83) (a) Andrus, M. B.; Hicken, E. J.; Stephens, J. C. Org. Lett. 2004, 6, 2289. (b) Andrus, M. B.; Hicken, E. J.; Stephens, J. C.; Bedke, D. K. J. Org. Chem. 2005, 70, 9470. (c) Andrus, M. B.; Hicken, E. J.; Stephens, J. C.; Bedke, D. K. J. Org. Chem. 2006, 71, 8651.
    Google ScholarLocate open access versionFindings
  • (84) Ooi, T.; Miki, T.; Maruoka, K. Org. Lett. 2005, 7, 191.
    Google ScholarFindings
  • (85) Ooi, T.; Fukumoto, K.; Maruoka, K. Angew. Chem., Int. Ed. 2006, 45, 3839. (86) (a) Bella, M.; Kobbelgaard, S.; Jørgensen, K. A. J. Am. Chem. Soc.
    Google ScholarLocate open access versionFindings
  • 2005, 127, 3670. (b) Kobbelgaard, S.; Bella, M.; Jørgensen, K. A. J. Org. Chem. 2006, 71, 4980.
    Google ScholarLocate open access versionFindings
  • (87) Poulsen, T. B.; Bernardi, L.; Bell, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 6551.
    Google ScholarLocate open access versionFindings
  • (88) Poulsen, T. B.; Bernardi, L.; Aleman, J.; Overgaard, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2007, 129, 441.
    Google ScholarLocate open access versionFindings
  • (89) Kumar, S.; Ramachandran, U. Tetrahedron: Asymmetry 2005, 16, 647.
    Google ScholarFindings
  • (90) Brozda, D.; Hoffman, K.; Rozwadowska, M. D. Heterocycles 2006, 69, 119.
    Google ScholarLocate open access versionFindings
  • (91) For recent reviews on catalytic asymmetric Michael reactions, see: (a) Krause, N.; Hoffman-Roder, A. Synthesis 2001, 171. (b) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. (c) Kanai, M.; Shibasaki M. In Catalytic Asymmetric Synthesis, second ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (d) Tomioka, K.; Nagaoka Y. In ComprehensiVe Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1.
    Google ScholarLocate open access versionFindings
  • (92) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hebrault, D. Org. Lett. 2000, 2, 2959.
    Google ScholarFindings
  • (93) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299.
    Google ScholarFindings
  • (94) Dere, R. T.; Pal, R. R.; Patil, P. S.; Salunkhe, M. M. Tetrahedron Lett. 2003, 44, 5351.
    Google ScholarLocate open access versionFindings
  • (95) Ooi, T.; Ohara, D.; Fukumoto, K.; Maruoka, K. Org. Lett. 2005, 7, 3195.
    Google ScholarFindings
  • (96) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2000, 2, 1097.
    Google ScholarFindings
  • (97) O’Donnell, M. J.; Delgado, F.; Domınguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
    Google ScholarLocate open access versionFindings
  • (98) Shibuguchi, T.; Mihara, H.; Kuramochi, A.; Sakuraba, S.; Ohshima, T.; Shibasaki, M. Angew. Chem., Int. Ed. 2006, 45, 4635. (99) (a) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535. (b) Arai, S.; Takahashi, F.; Tsuji, R.; Nishida, A. Heterocycles 2006, 67, 495.
    Google ScholarLocate open access versionFindings
  • (100) Arai, S.; Tokumaru, K.; Aoyama, T. Chem. Pharm. Bull. 2004, 52, 646.
    Google ScholarLocate open access versionFindings
  • (101) Lygo, B.; Allbutt, B.; Kirton, E. H. M. Tetrahedron Lett. 2005, 46, 4461.
    Google ScholarFindings
  • (102) Lee, Y.-J.; Lee, J.; Kim, M.-J.; Jeong, B.-S.; Lee, J.-H.; Kim, T.-S.; Lee, J.; Ku, J.-M.; Jew, S.-s.; Park, H.-g. Org. Lett. 2005, 7, 3207.
    Google ScholarLocate open access versionFindings
  • (103) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2004, 6, 3397.
    Google ScholarFindings
  • (104) Ceccarelli, R.; Insogna, S.; Bella, M. Org. Biomol. Chem. 2006, 4, 4281. (105) (a) Ooi, T.; Fujioka, S.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 11790. (b) Ooi, T.; Takada, S.; Fujioka, S.; Maruoka, K. Org. Lett. 2005, 7, 5143.
    Google ScholarLocate open access versionFindings
  • (106) Wang, X.; Kitamura, M.; Maruoka, K. J. Am. Chem. Soc. 2007, 129, 1038. (107) (a) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (b) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685.
    Google ScholarLocate open access versionFindings
  • (108) Mettath, S.; Srikanth, G. S. C.; Dangerfield, B. S.; Castle, S. L. J. Org. Chem. 2004, 69, 6489.
    Google ScholarLocate open access versionFindings
  • (109) Andrus, M. B.; Liu, J.; Ye. Z.; Cannon, J. F. Org. Lett. 2005, 7, 3861.
    Google ScholarFindings
  • (110) For a general review on asymmetric catalysis with quaternary ammonium fluoride, see: Ooi, T.; Maruoka, K. Acc. Chem. Res. 2004, 37, 526.
    Google ScholarLocate open access versionFindings
  • (111) (a) Arai, S.; Hasegawa, K.; Nishida, A. Tetrahedron Lett. 2004, 45, 1023. (b) Hasegawa, K.; Arai, S.; Nishida, A. Tetrahedron 2006, 62, 1390.
    Google ScholarLocate open access versionFindings
  • (112) Ooi, T.; Kameda, M.; Fujii, J.-i.; Maruoka, K. Org. Lett. 2004, 6, 2397.
    Google ScholarFindings
  • (113) Okada, A.; Shibuguchi, T.; Ohshima, T.; Masu, H.; Yamaguchi, K.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 4564.
    Google ScholarLocate open access versionFindings
  • (114) Palomo, C.; Oiarbide, M.; Laso, A.; Lopez, R. J. Am. Chem. Soc. 2005, 127, 17622.
    Google ScholarLocate open access versionFindings
  • (115) Fini, F.; Sgarzani, V.; Pettersen, D.; Herrera, R. P.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 7975.
    Google ScholarLocate open access versionFindings
  • (116) Fini, F.; Bernardi, L.; Herrera, R. P.; Pettersen, D.; Ricci, A.; Sgarzani, V. AdV. Synth. Catal. 2006, 348, 2043.
    Google ScholarLocate open access versionFindings
  • (117) For a review, see: Rosen, T. In ComprehensiVe Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 2, p 409.
    Google ScholarFindings
  • (118) Arai, S.; Tokumaru, K.; Aoyama, T. Tetrahedron Lett. 2004, 45, 1845.
    Google ScholarFindings
  • (119) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
    Google ScholarLocate open access versionFindings
  • (120) For reviews, see: (a) Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 1215. (b) Nemoto, T.; Ohshima, T.; Shibasaki, M. J. Synth. Org. Chem. Jpn. 2002, 60, 94.
    Google ScholarLocate open access versionFindings
  • (121) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623.
    Google ScholarLocate open access versionFindings
  • (122) Lygo, B.; To, D. C. M. Tetrahedron Lett. 2001, 42, 1343. (123) (a) Ye, J.; Wang, Y.; Liu, R.; Zhang, G.; Zhang, Q.; Chen, J.; Liang, X. Chem. Commun. 2003, 2714. (b) Ye, J.; Wang, Y.; Chen, J.; Liang, X. AdV. Synth. Catal. 2004, 346, 691. (124) (a) Adam, W.; Rao, P. B.; Degen, H.-G.; Saha-Moller, C. R. Tetrahedron: Asymmetry 2001, 12, 121. (b) Adam, W.; Rao, P. B.; Degen, H.-G.; Levai, A.; Patonay, T.; Saha-Moller, C. R. J. Org. Chem. 2002, 67, 259.
    Google ScholarLocate open access versionFindings
  • (125) Lygo, B.; To, D. C. M. Chem. Commun. 2002, 2360.
    Google ScholarLocate open access versionFindings
  • (126) Ooi, T.; Ohara, D.; Tamura, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 6844.
    Google ScholarLocate open access versionFindings
  • (127) Jew, S.-s.; Lee, J.-H.; Jeong, B.-S.; Yoo, M.-S.; Kim, M.-J.; Lee, Y.-J.; Lee, J.; Choi, S.-h.; Lee, K.; Lah, M. S.; Park, H.-g. Angew. Chem., Int. Ed. 2005, 44, 1383.
    Google ScholarLocate open access versionFindings
  • (128) Hori, K.; Tamura, M.; Tani, K.; Nishiwaki, N.; Ariga, M.; Tohda, Y. Tetrahedron Lett. 2006, 47, 3115.
    Google ScholarFindings
  • (129) Dorow, R. L.; Tymonko, S. A. Tetrahedron Lett. 2006, 47, 2493.
    Google ScholarFindings
  • (130) Lygo, B.; Gardiner, S. D.; To, D. C. M. Synlett 2006, 2063.
    Google ScholarLocate open access versionFindings
  • (131) For reviews, see: (a) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. (b) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
    Google ScholarFindings
  • (132) Murugan, E.; Siva, A. Synthesis 2005, 2022.
    Google ScholarFindings
  • (133) Bhunnoo, R. A.; Hu, Y.; Laine. D. I.; Brown, R. C. D. Angew. Chem., Int. Ed. 2002, 41, 3479.
    Google ScholarLocate open access versionFindings
  • (134) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496.
    Google ScholarLocate open access versionFindings
  • (135) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (136) (a) Ooi, T.; Uematsu, U.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 2548. (b) Ooi, T.; Uematsu, Y.; Fujimoto, J.; Fukumoto, K.; Maruoka, K. Tetrahedron Lett. 2007, 48, 1337.
    Google ScholarLocate open access versionFindings
  • (137) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Fini, F.; Pettersen, D.; Ricci, A. J. Org. Chem. 2006, 71, 9869.
    Google ScholarLocate open access versionFindings
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