Stereoselective Synthesis of α-Fluoro-γ-nitro Thioesters under Organocatalytic Conditions

被引：30

作者：

Cosimi, Elena ^{[1
]}

Saadi, Jakub ^{[1
]}

Wennemers, Helma ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Organ Chem Lab, Vladimir Prelog Weg 3, CH-8093 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 23期

基金：

瑞士国家科学基金会;

关键词：

ENANTIOSELECTIVE 1,4-ADDITION REACTIONS; HALF-THIOESTERS; PHARMACEUTICALS; NITROOLEFINS; NITROALKENES; HETEROCYCLES; FLUORINATION; CHEMISTRY; CENTERS; MONO;

D O I：

10.1021/acs.orglett.6b02795

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorinated monothiomalonates (F-MTMs) were used as building blocks for the stereoselective synthesis of organofluorine compounds. We present conjugate addition reactions between F-MTMs with nitroolefins that proceed under mild organocatalytic conditions and provide access to afluoro-y-nitro thioesters with adjacent tetrasubstituted and tertiary stereogenic centers. Only 1 mol % of a cinchona alkaloid urea catalyst is necessary to obtain the addition products in excellent yields and stereoselectivities. The methodology allowed for the straightforward synthesis of a fluorinated analogue of the PAR-2 agonist AC-264613.

引用

页码：6014 / 6017

页数：4

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