Communication

Single-Operation Deracemization of 3H-Indolines and Tetrahydroquinolines Enabled by Phase Separation

Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States
J. Am. Chem. Soc., 2013, 135 (38), pp 14090–14093
DOI: 10.1021/ja4082827
Publication Date (Web): September 11, 2013
Copyright © 2013 American Chemical Society

Abstract

Abstract Image

The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

Supporting Information


Procedures, spectral and X-ray crystallographic data. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 3,163 Times
Received 9 August 2013
Published online 11 September 2013
Published in print 25 September 2013
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