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

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

Key words

diamines - amino alcohols - 2-azadienes - reductive coupling - cross-coupling - fluoroarylation

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