Synthesis 2013; 45(15): 2101-2108
DOI: 10.1055/s-0032-1316921
special topic
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Asymmetric Amination of Allylic Trichloroacetimidates

Jeffrey S. Arnold
Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA   Email: hien-nguyen@uiowa.edu
,
Hien M. Nguyen*
Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA   Email: hien-nguyen@uiowa.edu
› Author Affiliations
Further Information

Publication History

Received: 22 February 2013

Accepted after revision: 20 March 2013

Publication Date:
30 April 2013 (online)

Abstract

A summary is presented of dynamic kinetic asymmetric transformations of racemic allylic trichloroacetimidates in the presence of chiral diene-ligated rhodium catalysts. The reaction is applicable to a wide variety of secondary and tertiary trichloroacetimidates containing aniline or benzylamine nucleophiles, affording nitrogen-containing tertiary and quaternary centers in good yields and with high levels of regio- and enantioselectivity. This catalytic method addresses many of the limitations previously associated with syntheses of these compounds.

Supporting Information

 
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