A Designed Approach to Enantiodivergent Enamine Catalysis

Juliet Macharia; Victor Wambua; Yun Hong; Lawrence Harris; Jennifer S Hirschi; Gary B Evans; Mathew J Vetticatt

doi:10.1002/anie.201703919

A Designed Approach to Enantiodivergent Enamine Catalysis

Angew Chem Int Ed Engl. 2017 Jul 17;56(30):8756-8760. doi: 10.1002/anie.201703919. Epub 2017 Jun 20.

Authors

Juliet Macharia¹, Victor Wambua¹, Yun Hong¹, Lawrence Harris², Jennifer S Hirschi¹, Gary B Evans², Mathew J Vetticatt¹

Affiliations

¹ Department of Chemistry, Binghamton University, Binghamton, NY, 13902, USA.
² Ferrier Research Institute, Victoria, University of Wellington, Wellington, New Zealand.

PMID: 28544165
DOI: 10.1002/anie.201703919

Abstract

The rational design and implementation of enantiodivergent enamine catalysis is reported. A simple secondary amine catalyst, 2-methyl-l-proline, and its tetrabutylammonium salt function as an enantiodivergent catalyst pair delivering the enantiomers of α-functionalized aldehyde products in excellent enantioselectivities. This novel concept of designed enantiodivergence is applied to the enantioselective α-amination, aldol, and α-aminoxylation/α-hydroxyamination reactions of aldehydes.

Keywords: aldehydes; amino acids; asymmetric catalysis; enantioselectivity; organocatalysis.

Publication types

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