title: Carbon nucleophiles in the Mitsunobu reaction. Mono- and dialkylation of bis(2,2,2-trifluoroethyl) malonates.
abstract: [formula: see text] 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.
authors.affiliation: Department of Chemistry, University of Nebraska--Lincoln, Lincoln, Nebraska 68588-0304, USA. jtakacs1@unl.edu
authors.forename: James M
authors.initials: JM
authors.lastname: Takacs
authors.forename: Zhenrong
authors.initials: Z
authors.lastname: Xu
authors.forename: Xun-tian
authors.initials: XT
authors.lastname: Jiang
authors.forename: Alexei P
authors.initials: AP
authors.lastname: Leonov
authors.forename: Gregory C
authors.initials: GC
authors.lastname: Theriot
mesh_terms: D000478:Alkylation; D005461:Fluorine; D008314:Malonates / Q000138:chemical synthesis*
chemical_list: D008314:Malonates; D005461:Fluorine