Mild and Diazo-Free Synthesis of Trifluoromethyl-Cyclopropanes Using Sulfonium Ylides

被引：28

作者：

Cyr, Patrick ^{[1
]}

Flynn-Robitaille, Joel ^{[1
]}

Boissarie, Patrick ^{[1
]}

Marinier, Anne ^{[1
,2
,3
]}

机构：

[1] Univ Montreal, Inst Res Immunol & Canc, Med Chem, Montreal, PQ H3C 3J7, Canada

[2] Univ Montreal, Fac Arts & Sci, Dept Chim, Montreal, PQ H3C 3J7, Canada

[3] Univ Montreal, Fac Med, Dept Pharmacol, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 07期

基金：

加拿大健康研究院;

关键词：

DISCOVERY; OPTIMIZATION; ALKENES; POTENT; ALPHA; ACID;

D O I：

10.1021/acs.orglett.9b00557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of several 1,1-disubstituted trifluoromethyl-cyclopropanes (TFCPs), known as tert-butyl bioisosteres, has been achieved from the reaction between trifluoromethylalkenes and unstabilized sulfonium ylides in yields of <= 97%. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing a commercially available reagent at low temperatures. The synthesis of cyclopropanes bearing other electron-withdrawing groups as well as trisubstituted TFCPs was also accomplished.

引用

页码：2265 / 2268

页数：4

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