Carbon Nucleophiles in the Mitsunobu Reaction. Mono- and Dialkylation of Bis(2,2,2-trifluoroethyl) Malonates
2002; American Chemical Society; Volume: 4; Issue: 22 Linguagem: Inglês
10.1021/ol0266626
ISSN1523-7060
AutoresJames M. Takacs, Zhenrong Xu, Xuntian Jiang, Alexei P. Leonov, Gregory C. Theriot,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoSimple 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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