Open Access2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines
Author(s) -
Steven J. Malcolmson,
Kangnan Li,
Xinxin Shao
Publication year - 2019
Publication title -
synlett
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.712
H-Index - 133
eISSN - 1437-2096
pISSN - 0936-5214
DOI - 10.1055/s-0037-1611770
Subject(s) - umpolung , synthon , chemistry , enamine , combinatorial chemistry , organocatalysis , amine gas treating , nucleophile , organic chemistry , enantioselective synthesis , catalysis
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.