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

James M. Takacs,* Zhenrong Xu, Xun-tian Jiang, Alexei P. Leonov, and Gregory C. Theriot
Department of Chemistry, University of NebraskaLincoln, Lincoln, Nebraska 68588-0304
Org. Lett., 2002, 4 (22), pp 3843–3845
DOI: 10.1021/ol0266626
Publication Date (Web): October 9, 2002
Copyright © 2002 American Chemical Society
*

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

, jtakacs1@unl.edu

Abstract

Abstract Image

Simple dialkyl malonate esters, for example diethyl malonate, exhibit relatively limited scope as carbon nucleophiles in the Mitsunobu dehydrative alkylation reaction. In contrast, bis(2,2,2-trifluoroethyl) malonate readily undergoes dehydrative alkylation with primary alcohols, and using only a slight excess of malonate gives monoalkylated product in good yield. Some secondary alcohols can also be employed, and bis(2,2,2-trifluoroethyl) malonates can be used in a second dehydrative alkylation to give dialkylated products in good to excellent yield.

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History

  • Published In Issue October 31, 2002
  • Received August 2, 2002

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