Open AccessCuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids
Author(s) -
Achim Link,
Yujing Zhou,
Stephen L. Buchwald
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c02064
Subject(s) - chemistry , catalysis , enantioselective synthesis , hydride , iridium , primary (astronomy) , combinatorial chemistry , carboxylic acid , organic chemistry , metal , physics , astronomy
The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides.