Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

被引：78

作者：

Kalow, Julia A. ^{[1
]}

Doyle, Abigail G. ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

TETRAHEDRON | 2013年 / 69卷 / 27-28期

基金：

美国国家科学基金会;

关键词：

Asymmetric catalysis; Fluorination; Aziridine opening; Cooperative catalysis; beta-Fluoroamine; ASYMMETRIC CATALYSIS; MESO-AZIRIDINES; PIPERIDINYL AZIRIDINE; BETA-FLUOROAMINES; DESYMMETRIZATION; COMPLEXES; EPOXIDES; FLUORINATION; STRATEGY; ACCESS;

D O I：

10.1016/j.tet.2013.01.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5702 / 5709

页数：8

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