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Asymmetric Allylsilane Additions to Enantiopure N ‐Acylhydrazones with Dual Activation by Fluoride and In(OTf) 3
Author(s) -
Friestad Gregory K.,
Ding Hui
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20011203)40:23<4491::aid-anie4491>3.0.co;2-8
Subject(s) - enantiopure drug , trifluoromethanesulfonate , dual (grammatical number) , chemistry , hydrazone , stereoselectivity , fluoride , computer science , organic chemistry , philosophy , enantioselective synthesis , catalysis , inorganic chemistry , linguistics
A mild, convenient, and stereoselective addition of allylsilanes to enantiopure N ‐acylhydrazones occurs at room temperature upon complementary activation of both the allylsilane and the hydrazone (see scheme; OTf = trifluoromethanesulfonate). The reaction provides a new mode of acyclic stereocontrol for the asymmetric synthesis of homoallylic amines.