Esterification of 3-hydroxy-2-naphthoic acid with homologous primary and secondary alkenyl alcohols with different chain lengths in the presence of N,N'-carbonyldiimidazole (CDI) and 1,8-diazabicyclo[ 5.4.0]undec-7-ene (DBU) in N,N-dimethylformamide gave the corresponding esters.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Pd complexes have been obtained from linear and cross-linked copolymers ofR,S-, R-, andS-1-(4-vinylphenyl)ethylamine (1) with styrene and divinylbenzene. Reduction of these compounds gave catalysts which were active in the reductive solvolysis of α-acetaminocinnamic acid azlactone (2) and hydrogenation of the solvolysis products α-acetamidocinnamic acid (ACA), its esters, and its 1-phenylethylamide. The catalysts showed no enantioselective properties in the reductive hydrolysis, but were more active than the catalyst obtained in the absence of the polymer (the “monomeric” analog). The use of polymeric catalysts has shown that, in reductive aminolysis, the chiral nucleophile plays the dominant part in determining the stereoselectivity of the reaction, rather than the chiral ligand of the catalytic complex. The polymer matrix stabilizes the low-valent state of the palladium in the complex. In the hydrogenation of ACA and its esters, the catalyst on the cross-linked polymer is much more active than its “monomeric” analog, but showed no enantioselectivity. Hydrogenation of acetamidocinnamic acidR-andS-1-phenylethylamides on a chiral Pd-polymer catalyst occurred with double asymmetric induction.

On the base of linear and crosslinked copolymers of S- and R-1-[4-vinylphenyl]ethylamine (monomer A) with styrene (monomer B) and divinylbenzene the compositionally homogeneous chiral palladium-polymer catalysts containing 25-26 mol % of monomer A unites have been synthesized. The constants of copolymerization r(A)=0.10 and r(B)=0.69 are determined. The interaction of PdCl2 with copolymers is shown to result mainly in the formation of interchain biligand complexes of Pd with amine groups. A polymer matrix stabilizes the low-valent (after reduction) state of palladium in these complexes. Application of polymer catalysts permitted to establish the main contribution into the stereoselectivity of the chiral nucleophyl, but not of chiral ligand of the catalytic complex in the reaction of reductive aminolysis of azlactones under the action of chiral amines. Chiral polymer catalyst manifests the double asymmetric induction effect in the reaction of hydration of R- and S-1-phenylethylamides of acetaminocinnamic acid.

The infrared and Raman Spectra of saturated and unsaturated δ2-oxazolin-5-ones (azlactones) have been studied for CCl2, CHCl3, i-PrOH, and t-BuOH solutions and for the solid phase. Frequency assignments have been made for C=O bond stretching in the region 1825–1770 cm−1 and for a mixed C=C and C=N vibration at 1690–1550 cm−1. All of the azlactones showed an intense, characteristic absorption in a narrow range near 900 cm−1 which was assigned to a deformation vibration of the oxazolone ring.

Catalytic reductive aminolysis of the azalactones of N-acyl-p-difluoromethoxy-α-aminocinnamic acid in dimethoxyethane, isopropanol, and tert-butanol proceeds stereoselectively, leading to the α-phenylethylamides of N-acyl-p-difluoromethoxyphenylalanine with a 3–55% excess of the S,S-diastereomer.

AbstractThe hitherto unknown title compounds (IV) and (VIII) are prepared in two ways.

ChemInformVolume 19, Issue 9 Preparative Organic Chemistry ChemInform Abstract: Catalytic Asymmetric Synthesis of Lysine by Hydrogenation of α-Nitrocaprolactam. E. I. KLABUNOVSKII, E. I. KLABUNOVSKII Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorD. D. GOGOLADZE, D. D. GOGOLADZE Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. S. LEVITINA, E. S. LEVITINA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. I. KARPEISKAYA, E. I. KARPEISKAYA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorL. F. GODUNOVA, L. F. GODUNOVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorL. I. KAIGORODOVA, L. I. KAIGORODOVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorG. O. CHIVADZE, G. O. CHIVADZE Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this author E. I. KLABUNOVSKII, E. I. KLABUNOVSKII Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorD. D. GOGOLADZE, D. D. GOGOLADZE Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. S. LEVITINA, E. S. LEVITINA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. I. KARPEISKAYA, E. I. KARPEISKAYA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorL. F. GODUNOVA, L. F. GODUNOVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorL. I. KAIGORODOVA, L. I. KAIGORODOVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorG. O. CHIVADZE, G. O. CHIVADZE Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this author First published: March 1, 1988 https://doi.org/10.1002/chin.198809113Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume19, Issue9March 1, 1988 RelatedInformation

ChemInformVolume 19, Issue 4 Natural Products ChemInform Abstract: Asymmetric Synthesis by Catalytic Reductive Aminolysis of p-Fluoro-α- acetylaminocinnamic Acid Azlactone. Part 18. Preparation of (S)-(-)-p- Fluorophenylalanine. L. F. GODUNOVA, L. F. GODUNOVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. I. KARPEISKAYA, E. I. KARPEISKAYA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. S. LEVITINA, E. S. LEVITINA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. I. KLABUNOVSKII, E. I. KLABUNOVSKII Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorYU. L. YAGUPOL'SKII, YU. L. YAGUPOL'SKII Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorM. T. KOLYCHEVA, M. T. KOLYCHEVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this author L. F. GODUNOVA, L. F. GODUNOVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. I. KARPEISKAYA, E. I. KARPEISKAYA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. S. LEVITINA, E. S. LEVITINA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorE. I. KLABUNOVSKII, E. I. KLABUNOVSKII Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorYU. L. YAGUPOL'SKII, YU. L. YAGUPOL'SKII Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this authorM. T. KOLYCHEVA, M. T. KOLYCHEVA Inst. org. khim. im. Zelinskogo AN SSSR, MoskvaSearch for more papers by this author First published: January 26, 1988 https://doi.org/10.1002/chin.198804349Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume19, Issue4January 26, 1988 RelatedInformation

Hydrogenation of α-nitrpcaprolactam by treatment with a Pd catalyst in the presence of S-α-phenylethylamine in aprotic solvents proceeds via azoxycaprolactam as an intermediate.

In reductive aminolysis of p-fluoroacetaminocinnamic acid azalactone by S-(-)-a-phenylethylamine in the presence of PdCl2 and H2 in dimethoxyethane or isopropyl alcohol, N-acetyl-p-fluorophenylalanine phenylethylamide was formed with 28 and 46% excesses of the SS diastereomer, respectively, the hydrolysis of which, after crystallization, afforded optically pure S-(-)-p-fluorophenylalanine.

PMR examination of deuterated acetylphenylalanine α-phenylethylatnide and the methyl esters of acetyl- and benzoylphenylalanine, obtained by the reductive solvolysis of 2-methyl- and 2-phenyl-4-benzylideneoxazolin-5-ones, has shown that in the reduction of oxazolinones the hydrogen undergoes cis- and trans-addition in a ratio of 1∶1.

Reaction of 2-methyl-4-benzylideneoxazol-5-one with a zerovalent palladium complex containing S-(-)-α-phenylethylamine as ligand, in chloroform or dichloromethane as solvent, gives a heteroligand complex which is a reactive intermediate in reductive aminolysis,