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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 4
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Original Articles

THE REACTION OF β-KETOACIDS WITH ALLYLBORONATES

George W. Kabalka Departments of Chemistry & Radiology, The University of Tennessee, Knoxville, TN, 37996-1600, U.S.A.
,
Kathy Yang Departments of Chemistry & Radiology, The University of Tennessee, Knoxville, TN, 37996-1600, U.S.A.
&
Zhe Wang DuPont Pharmaceuticals, Chambers Works, Deepwater, NJ, 08023, U.S.A.
Pages 511-517 | Received 22 May 2000, Published online: 16 Aug 2006
 
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Abstract

Allylboronates react with β-ketoacids to yield tertiary homoallylic β-hydroxycarboxylic acids. The reaction presumably proceeds via a bicyclic transition state. The β-carboxylic substituent enhances the rate of the reaction.

ACKNOWLEDGMENTS

We thank the US Department of Energy and the Robert H. Cole Foundation for support of this research.

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