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Paper | Special issue | Vol 86, No. 2, 2012, pp. 1483 - 1494
Published online: 22nd November, 2012
DOI: 10.3987/COM-12-S(N)129
ASYMMETRIC INTRAMOLECULAR CONJUGATE ADDITION OF α-AMINO ACID DERIVATIVES VIA RACEMIZATION-FREE EQUILIBRIUM OF INTERMEDIARY CHIRAL ENOLATES

Daiki Monguchi, Tomoyuki Yoshimura, Kazuyuki Irie, Kazuhiro Hayashi, Swapan Majumdar, Takahiro Sasamori, Norihiro Tokitoh, and Takeo Kawabata*

*Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan

Abstract

A highly enantioselective route to a multi-substituted indoline derivative via intramolecular conjugate addition of an α-amino acid derivative has been developed. Enantioselectivity of the reaction was almost independent from the temperature, while the diastereoselectivity was totally dependent on the temperature. High diastereomeric ratios observed at the higher temperatures were assumed to be the results from an equilibrium process between axially chiral enolate intermediates.

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