Zinc enolates derived from an ester and a lactone, 1 and 4, were found to have enhanced reactivity over the corresponding lithium enolates in asymmetric nitroolefination.
Diastereotopic olefins were differentiated in iodolactonization with concomitant face differentiation using (2R,5R)-bis(methoxymethyl)pyrrolidine as a chiral auxiliary to afford chiral lactones in enantioselective manner.
AbstractThe reaction of the zinc enolates derived from the lactones (I) and the chiral nitro enamines (II) affords the α,α‐disubstituted lactones (III) with high e.e.
ChemInformVolume 19, Issue 1 Preparative Organic Chemistry ChemInform Abstract: Stereoselective Nitroolefination of Active Methine of Various Carbonyl Compounds with β-Nitroenamines. M. NODE, M. NODE Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this authorH. NAGASAWA, H. NAGASAWA Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this authorY. NANIWA, Y. NANIWA Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this authorK. FUJI, K. FUJI Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this author M. NODE, M. NODE Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this authorH. NAGASAWA, H. NAGASAWA Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this authorY. NANIWA, Y. NANIWA Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this authorK. FUJI, K. FUJI Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, JapanSearch for more papers by this author First published: January 5, 1988 https://doi.org/10.1002/chin.198801126Read 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, Issue1January 5, 1988 RelatedInformation
AbstractA new method for a chiral synthesis of quaternary carbon centers via the addition‐elimination process is described: Reaction of enolates (I) or (IV) with the nitroenamines (II) provides the optically active compounds (III) or (V), respectively.