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