Issue 7, 2014

Catalytic stereospecific allylation of protected hydrazines with enantioenriched primary allylic amines

Abstract

An unprecedented allylation reaction of protected hydrazines with enantioenriched allylic amines has been developed in a stereospecific manner with net stereoretention. A wide variety of protected hydrazines underwent palladium/acid-catalyzed allylation with highly enantioenriched primary allylic amines to give structurally diverse N-allylhydrazines in moderate to excellent yields with extremely high regioselectivity and complete retention of the configuration. Importantly, the reaction exhibits high atom-economy by yielding ammonia as the sole byproduct.

Graphical abstract: Catalytic stereospecific allylation of protected hydrazines with enantioenriched primary allylic amines

Supplementary files

Article information

Article type
Research Article
Submitted
27 May 2014
Accepted
04 Jul 2014
First published
07 Jul 2014

Org. Chem. Front., 2014,1, 812-816

Catalytic stereospecific allylation of protected hydrazines with enantioenriched primary allylic amines

Y. Wang, J. Xu, Y. Gu and S. Tian, Org. Chem. Front., 2014, 1, 812 DOI: 10.1039/C4QO00155A

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