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α-Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups

Author:
Qin, Shuanglin, Liu, Shuangwei, Cao, Yuting, Li, Jiangnan, Chong, Chuanke, Liu, Tongtong, Luo, Yunhao, Hu, Jiyun, Jiang, Shende, Zhou, Honggang, Yang, Guang, Yang, Cheng
Source:
Organic letters 2018 v.20 no.5 pp. 1350-1354
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, diastereoselectivity, imines, ketones, regioselectivity, synergism
Abstract:
This study developed a facile and efficient synthetic strategy to construct quaternary chiral centers at the α-position of imines and ketones. High regioselectivity and diastereoselectivity were achieved through the synergetic effect of electron-withdrawing directing groups and N-tert-butyl sulfinamide as chiral auxiliaries. Either of them could be removed under the optimized conditions without any epimerization.
Agid:
6083559