Carbon nucleophiles in the Mitsunobu reaction. Mono-and dialkylation of bis(2,2,2-trifluoroethyl) malonates

被引：24

作者：

Takacs, JM ^{[1
]}

Xu, ZR ^{[1
]}

Jiang, XT ^{[1
]}

Leonov, AP ^{[1
]}

Theriot, GC ^{[1
]}

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 22期

关键词：

D O I：

10.1021/ol0266626

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3843 / 3845

页数：3

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