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Carbon Nucleophiles in the Mitsunobu Reaction. Mono and Dialkylation of Bis(2,2,2-trifluorethyl) Malonates

James M. Takacs*, Zhenrong Xu, Xun-tian Jiang, Alexei P. Leonov and Gregory C. Theriot

*Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA, Email: jtakacs1unl.edu

J. M. Takacs, Z. Xu, X.-T. Jiang, A. P. Leonov, G. C. Theriot, Org. Lett., 2002, 4, 3843-3845.

DOI: 10.1021/ol0266626 (free Supporting Information)


Abstract

Simple dialkyl malonate esters exhibit limited scope as carbon nucleophiles in the Mitsunobu reaction. In contrast, bis(2,2,2-trifluoroethyl) malonates readily undergo dehydrative alkylation with primary and some secondary alcohols.

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Key Words

Active Methylenes, Allylation, Mitsunobu Reaction


ID: J54-Y2002-180