Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides

被引：69

作者：

Haj, Moriana K. ^{[1
]}

Banik, Steven M. ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 13期

关键词：

XENON DIFLUORIDE; ORGANIC-COMPOUNDS; ELEMENTAL FLUORINE; ALKENES; AMINOFLUORINATION; STEREOCHEMISTRY; DIAMINATION; IMPACT;

D O I：

10.1021/acs.orglett.9b00938

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantio- and diastereoselective synthesis of 1,2-difluorides via chiral aryl iodide-catalyzed difluorination of cinnamamides is reported. The method uses HF-pyridine as a fluoride source and mCPBA as a stoichiometric oxidant to turn over catalyst, and affords compounds containing vicinal, fluoride-bearing stereocenters. Selectivity for 1,2-difluorination versus a rearrangement pathway resulting in 1,1-difluorination is enforced through anchimeric assistance from a N-tert-butyl amide substituent.

引用

页码：4919 / 4923

页数：5

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