Sulfur ylides via decarboxylation of carboxymethylsulfonium betaines: A novel and mild protocol for the preparation of oxiranes
Sulfur ylides via decarboxylation of carboxymethylsulfonium betaines: A novel and mild protocol for the preparation of oxiranes
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DOI：
10.1021/ol034612a
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发表时间：
2003-06-26
期刊：
影响因子：
5.2
通讯作者：
Lewis, DL
中科院分区：
文献类型：
--
作者：
Forbes, DC;Standen, MC;Lewis, DL
介绍了一种新的硫叶立德的合成方法。整个过程包括羧甲基锍甜菜碱的热脱羧，得到硫叶立德，在醛的存在下，得到相应的末端环氧乙烷。发现产率与芳基醛的缺电子相关。在醛存在下原位生成甜菜碱成功地以中等产率提供了所需的环氧乙烷，从而证明了催化方法的可行性。
A novel protocol for the generation of sulfur ylides is described. The overall process involves thermal decarboxylation of a carboxymethyl-sulfonium betaine to give a sulfur ylide that, in the presence of an aldehyde, affords the corresponding terminal oxirane. Yields were found to correlate with the electron deficiency of the aryl aldehyde. In situ generation of betaine in the presence of an aldehyde successfully afforded the desired oxirane in moderate yield, thus demonstrating the feasibility of a catalytic process.