Synlett 2012; 23(6): 863-866
DOI: 10.1055/s-0031-1290485
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© Georg Thieme Verlag Stuttgart · New York

LiAlH4-Induced Reductive Dephosphonylation of α,α-Dialkyl Triethyl β-Phosphonyl Esters: Mechanistic Study and Synthetic Application

Jia-Liang Zhu*
Department of Chemistry, National Dong Hwa University, Hualien 974, Taiwan, R.O.C., Fax: +886(3)8633570   Email: jlzhu@mail.ndhu.edu.tw
,
Jr-Sheng Bau
Department of Chemistry, National Dong Hwa University, Hualien 974, Taiwan, R.O.C., Fax: +886(3)8633570   Email: jlzhu@mail.ndhu.edu.tw
,
You-Cheng Shih
Department of Chemistry, National Dong Hwa University, Hualien 974, Taiwan, R.O.C., Fax: +886(3)8633570   Email: jlzhu@mail.ndhu.edu.tw
› Author Affiliations
Further Information

Publication History

Received: 10 January 2012

Accepted after revision: 24 January 2012

Publication Date:
28 February 2012 (online)


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Abstract

Treatment of α,α-dialkyl triethyl β-phosphonyl esters with LiAlH4 in CH2Cl2–THF caused the one-pot dephosphonylation and reduction to yield the corresponding primary alcohols bearing a controllable β secondary carbon center. Mechanistic study has revealed that the LiAlH4-induced dephosphonylation should occur first with the assistance of the carboxylate group, and the hydrogen source of the resultant new C–H bond is LiAlH4.