Enantioselective Intramolecular C-H Insertion Reactions of α-Diazo β-Keto  Esters Catalyzed by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-phenylalaninate]:  The Effect of the Substituent at the Insertion Site on Enantioselectivity

Shun-ichi Hashimoto; Nobuhide Watanabe; Shiro Ikegami

doi:10.1055/s-1994-22852

Synlett 1994; 1994(5): 353-355
DOI: 10.1055/s-1994-22852

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Enantioselective Intramolecular C-H Insertion Reactions of α-Diazo β-Keto Esters Catalyzed by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-phenylalaninate]: The Effect of the Substituent at the Insertion Site on Enantioselectivity

Shun-ichi Hashimoto^* , Nobuhide Watanabe, Shiro Ikegami

^*Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-01, Japan

Abstract

PDF Download All articles of this category

The enantioselectivity in dirhodium(II) tetrakis[N-phthaloyl-(S) -phenylalaninate]-catalyzed cyclization of α-diazo β-keto 2,4-dimethyl-3-phenyl esters possessing substituted phenyl or vinyl groups at the insertion site was studied. The substituent effects on enhancement of the enantioselectivity were even more pronounced with the vinyl group than with the phenyl group, though 80% ee could be achieved with both of the (E)-conjugated ester and p-trifluoromethanesulfonyloxyphenyl groups.

PDF (217 kb)