Synlett 2019; 30(11): 1253-1268
DOI: 10.1055/s-0037-1611770
synpacts
© Georg Thieme Verlag Stuttgart · New York

2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines

Steven J. Malcolmson*
Department of Chemistry, Duke University, NC 27708, USA
,
Kangnan Li
,
Xinxin Shao
› Author Affiliations
Our research was generously supported by the National Institutes of Health (GM124286), the American Chemical Society PRF (57565-DNI1), and Duke University.
Further Information

Publication History

Received: 02 February 2019

Accepted after revision: 05 March 2019

Publication Date:
26 March 2019 (online)

Abstract

The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.

1 Introduction

2 Background: Umpolung Strategies for Preparing Chiral Amines

3 Background: 2-Azadienes

4 Reductive Couplings of 2-Azadienes

5 Fluoroarylations of gem-Difluoro-2-azadienes

6 Summary and Outlook

 
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