Highly Stereoselective Intramolecular Carbofluorination of Internal α,β-Ynones Promoted by Selectfluor

被引：11

作者：

Zhu, Bingbin ^{[1
]}

Han, Hang ^{[2
]}

Su, Wei-Ke ^{[1
]}

Yan, Boan ^{[2
]}

Li, Zhi ^{[2
]}

Yu, Chuanming ^{[2
]}

Jiang, Xinpeng ^{[2
]}

机构：

[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Peoples R China

[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 11期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC-SYNTHESIS; DIPEPTIDE ISOSTERES; FLUORINE; FLUOROOLEFIN;

D O I：

10.1021/acs.orglett.1c01441

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a metal-free intramolecular carbofluorination protocol for the synthesis of tetrasubstituted monofluoroalkenes from internal alpha,beta-ynones and Selectfluor with both high stereoselectivity and broad functional group tolerance. The chelation between tetrafluoroborate anion and the oxygen present in the aldehyde group rendered the reaction highly stereoselective, with the tetrafluoroborate serving as the direct fluorine source. Therefore, with addition of sodium tetrafluoroborate, Selectfluor could be reused several times without sacrificing reactivity.

引用

页码：4488 / 4492

页数：5

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