Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes

被引：128

作者：

Mennie, Katrina M. ^{[1
]}

Banik, Steven M. ^{[1
]}

Reichert, Elaine C. ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 14期

关键词：

ORGANOCATALYTIC ALPHA-FLUORINATION; INTERMOLECULAR AMINOFLUORINATION; ACCESS; DIFLUORINATION; AZIRIDINES; ACID;

D O I：

10.1021/jacs.8b02143

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselective synthesis of syn-beta-fluoroaziridine building blocks via chiral aryl iodide catalyzed fluorination of allylic amines is reported. The method employs HF pyridine as a nucleophilic fluoride source together with mCPBA as a stoichiometric oxidant, and affords access to arylethylamine derivatives featuring fluorine-containing stereocenters in high diastereo- and enantioselectivity. Catalyst-controlled diastereoselectivity in the fluorination of chiral allylic amines enabled the preparation of highly enantioenriched 1,3-difluoro-2-amines bearing three contiguous stereocenters. The enantioselective catalytic method was applied successfully to other classes of multifunctional alkene substrates to afford anti-beta-fluoropyrrolidines, as well as a variety of 1,2-oxyfluorinated products.

引用

页码：4797 / 4802

页数：6

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