Rhodium-Catalyzed Asymmetric Synthesis of β-Branched Amides

Zhao Wu; Joshua D Laffoon; Trang T Nguyen; Jacob D McAlpin; Kami L Hull

doi:10.1002/anie.201610500

Rhodium-Catalyzed Asymmetric Synthesis of β-Branched Amides

Angew Chem Int Ed Engl. 2017 Jan 24;56(5):1371-1375. doi: 10.1002/anie.201610500. Epub 2016 Dec 27.

Authors

Zhao Wu¹, Joshua D Laffoon¹, Trang T Nguyen¹, Jacob D McAlpin¹, Kami L Hull¹

Affiliation

¹ Department of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews, Urbana, IL, 61821, USA.

PMID: 28026091
DOI: 10.1002/anie.201610500

Abstract

A general asymmetric route for the one-step synthesis of chiral β-branched amides is reported through the highly enantioselective isomerization of allylamines, followed by enamine exchange, and subsequent oxidation. The enamine exchange allows for a rapid and modular synthesis of various amides, including challenging β-diaryl and β-cyclic.

Keywords: amidation; asymmetric isomerization; β-branched amides.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't