Chemistry and Physics Faculty Articles

Title

Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes

Document Type

Article

Publication Date

10-10-2018

Publication Title

Journal of the American Chemical Society

ISSN

0002-7863

Volume

140

Issue/No.

40

First Page

12687

Last Page

12690

Abstract

A new reactivity in organocatalysis is proposed to account for the coupling of carboxylic acids to α-branched aldehydes by combining primary amine catalysis and an oxidant. The developed methodology is an enantioselective α-coupling of aromatic and aliphatic carboxylic acids to α-branched aldehydes and proceeds in high yields (up to 97%) and for most examples good enantioselectivities (up to 92% ee). On the basis of experimental and mechanistic observations, the role of the primary amine catalyst is discussed.

Comments

©2018 American Chemical Society

ORCID ID

0000-0002-0566-0820

ResearcherID

V-6501-2018

DOI

10.1021/jacs.8b07394

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Peer Reviewed

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