Carbon nucleophiles in the Mitsunobu reaction. Mono- and dialkylation of bis(2,2,2-trifluoroethyl) malonates |
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Authors: | Takacs James M Xu Zhenrong Jiang Xun-tian Leonov Alexei P Theriot Gregory C |
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Institution: | Department of Chemistry, University of Nebraska--Lincoln, Lincoln, Nebraska 68588-0304, USA. jtakacs1@unl.edu |
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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. |
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