Journal
ORGANIC LETTERS
Volume 4, Issue 22, Pages 3843-3845Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0266626
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- NCRR NIH HHS [1-510-RR-06307] Funding Source: Medline
- NIGMS NIH HHS [GM34927] Funding Source: Medline
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graphic 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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