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Article

Alkylation of H-Phosphinate Esters under Basic Conditions

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Isabelle Abrunhosa-Thomas, Claire E. Sellers, and Jean-Luc Montchamp*

Department of Chemistry, Texas Christian University, TCU Box 298860, Fort Worth, Texas 76129

J. Org. Chem., 2007, 72 (8), pp 2851–2856

DOI: 10.1021/jo062436o

Publication Date (Web): March 13, 2007

To whom correspondence should be addressed. Fax: (+1) 817 257 5851. Phone: (+1) 817 257 6201.

, j.montchamp@tcu.edu

Abstract

An efficient and general procedure was developed for the direct alkylation of H-phosphinate esters with LHMDS at low temperature. The simplicity of the reaction allows the use of various H-phosphinate esters and takes place with a wide range of electrophiles. The approach can be employed to access some GABA analogues or precursors to GABA analogues. The isolated yields are moderate to good. This is the first report of an alkylation with a secondary iodide or a primary chloride.

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Published In Issue April 13, 2007
Received November 27, 2006

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Article

Alkylation of H-Phosphinate Esters under Basic Conditions