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Asymmetric Allylsilane Additions to Enantiopure N‐Acylhydrazones with Dual Activation by Fluoride and In(OTf)3
Journal article   Peer reviewed

Asymmetric Allylsilane Additions to Enantiopure N‐Acylhydrazones with Dual Activation by Fluoride and In(OTf)3

Gregory K Friestad and Hui Ding
Angewandte Chemie International Edition, Vol.40(23), pp.4491-4493
12/03/2001
DOI: 10.1002/1521-3773(20011203)40:23<4491::AID-ANIE4491>3.0.CO;2-8
PMID: 12404456

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Abstract

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.
amines chiral auxiliaries asymmetric synthesis allylation hydrazones

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