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Highly Enantioselective Direct Alkylation of Arylacetic Acids with Chiral Lithium Amides as Traceless Auxiliaries

Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States
J. Am. Chem. Soc., 2011, 133 (31), pp 11936–11939
DOI: 10.1021/ja205107x
Publication Date (Web): July 11, 2011
Copyright © 2011 American Chemical Society

Abstract

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A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

Detailed experimental procedures, characterization data, copies of 1H and 13C NMR spectra, and HPLC traces for all compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 6,569 Times
Received 2 June 2011
Published online 11 July 2011
Published in print 10 August 2011
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