Exceptionally mild, high-yield synthesis of α-fluoro acrylates

被引：55

作者：

Zajc, Barbara ^{[1
]}

Kake, Shivani ^{[1
]}

机构：

[1] CUNY City Coll, Dept Chem, New York, NY 10031 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 20期

关键词：

D O I：

10.1021/ol0616236

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel achiral and chiral alkyl alpha-(1,3-benzothiazol-2-ylsulfonyl)-alpha-fluoroacetates can be readily synthesized by metalation-fluorination of (1,3-benzothiazol- 2-ylsulfonyl) acetates. DBU-mediated condensations of these fluorinated synthons with aldehydes proceed in a facile manner at 0 degrees C or at room temperature giving high yields of alpha-fluoro acrylates. Ketones are unreactive under these conditions. The presence of fluorine renders the synthon substantially more reactive compared to the unfluorinated analogue. Reactivity of alpha-(1,3-benzothiazol-2-ylsulfonyl)-rfluoroacetate and the Horner-Wadsworth-Emmons reagent (EtO)(2)P(O)CHFCOOEt has also been compared.

引用

页码：4457 / 4460

页数：4

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