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Letter

Synthesis of Tertiary α-Hydroxy Acids by Silylene Transfer to α-Keto Esters

Supporting Info

Brett E. Howard and K. A. Woerpel*

Department of Chemistry, University of California, Irvine, California 92697-2025

Org. Lett., 2007, 9 (22), pp 4651–4653

DOI: 10.1021/ol702148x

Publication Date (Web): October 2, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kwoerpel@uci.edu

Abstract

α-Keto esters can be converted into α-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6π-electrocyclization, Ireland−Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted α-keto ester substrates as well as an α-imino ester.

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Published In Issue October 25, 2007
Received August 31, 2007

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Letter

Synthesis of Tertiary α-Hydroxy Acids by Silylene Transfer to α-Keto Esters

Abstract

Tools

SciFinder Links

History

Recommend & Share

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