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Bifunctional Homoallylic Carbamates from Chiral Silane Additions to in Situ Generated N-Acyl Iminium Ions

Author:
Wu, Jie, Zhu, Kai-Cheng, Yuan, Ping-Wei, Panek, James S.
Source:
Organic letters 2012 v.14 no.14 pp. 3624-3627
ISSN:
1523-7052
Subject:
Lewis acids, carbamates, chemical reactions, chemical structure, ions, lactams, silane
Abstract:
Homoallylic carbamates bearing an α,β-unsaturated ester or an allylic carbonate were generated respectively utilizing novel chiral silanes through Lewis acid promoted asymmetric aminocrotylation. Those bifunctional building blocks could further undergo Michael addition or cyclization to selectively form functionalized lactams, azetidines, and tetrahydropyrimidinones.
Agid:
5784071