Issue 20, 2020

Kinetic resolution of 2H-azirines via Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

Abstract

A highly efficient kinetic resolution of racemic 2H-azirines has been achieved by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. With an (S,Sp)-Ph-Phosferrox/Cu(MeCN)4BF4 complex as the catalyst, optically pure 2H-azirines were obtained with excellent enantioselectivities (up to 99% ee) and high resolution efficiency (S factors up to 845). Meanwhile, this process provided a direct approach to synthesize structurally novel 1,3-diazabicyclo[3.1.0]hexane derivatives with excellent enantioselectivities (94–99% ee).

Graphical abstract: Kinetic resolution of 2H-azirines via Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

Supplementary files

Article information

Article type
Research Article
Submitted
03 Jul 2020
Accepted
18 Sep 2020
First published
18 Sep 2020

Org. Chem. Front., 2020,7, 3247-3252

Kinetic resolution of 2H-azirines via Cu(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

H. Deng, T. Liu, Z. Ding, W. Yang, X. Luo and W. Deng, Org. Chem. Front., 2020, 7, 3247 DOI: 10.1039/D0QO00789G

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