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Asymmetric Synthesis of trans-2,3-Disubstituted Indoline Derivatives

Author:
Kang, Kyoung Hee, Do, Junghwan, Park, Yong Sun
Source:
Journal of organic chemistry 2012 v.77 no.1 pp. 808-812
ISSN:
1520-6904
Subject:
Lewis acids, Lewis bases, aldehydes, methodology, organic chemistry
Abstract:
A novel method for asymmetric synthesis of trans-2,3-disubstituted indolines has been developed. The strategy involves the (−)-sparteine-mediated electrophilic substitution of 2-benzyl N-pivaloylaniline with aromatic or α,β-unsaturated aldehydes and subsequent intramolecular nucleophilic substitution. The simple protocol for two-step process can produce highly enantioenriched indolines 3a–o up to 98:2 er.
Agid:
5498707