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

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 sulfinam...

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Veröffentlicht in:Organic letters 2018-03, Vol.20 (5), p.1350-1354
Hauptverfasser: Qin, Shuanglin, Liu, Shuangwei, Cao, Yuting, Li, Jiangnan, Chong, Chuanke, Liu, Tongtong, Luo, Yunhao, Hu, Jiyun, Jiang, Shende, Zhou, Honggang, Yang, Guang, Yang, Cheng
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00105