Asymmetric aziridination of 1,3-dienes catalyzed by bisoxazoline-copper complexes

Chirality
Linge MaJiaxi Xu

Abstract

The asymmetric aziridination of 1,3-dienes catalyzed by bisoxazoline-CuOTf complexes with PhI=NTs as a nitrene precursor has been achieved in moderate yields with up to >99:1 regioselectivity, up to >99% diastereoselectivity, and up to 80% enantioselectivity. alpha,beta,gamma,delta-Unsaturated ketones usually produced cis-gamma,delta-aziridinated products, while 1,4-diphenyl-1,3-butadiene afforded both of cis- and trans-aziridine derivatives as major products by the use of different bisoxazoline ligands. The configuration of cis-aziridine derivatives was proposed on the basis of the reaction mechanism.

Citations

Jan 26, 2013·Chemical Reviews·Bagher Eftekhari-SisAli Akbari
Aug 7, 2012·Angewandte Chemie·Akira YoshimuraViktor V Zhdankin
Aug 19, 2010·Angewandte Chemie·Josep LlaveriaPedro J Pérez
Sep 3, 2011·Chemistry : a European Journal·Qiong WuJianrong Zhou
Nov 29, 2011·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Joyce Wei Wei ChangPhilip Wai Hong Chan
Jul 21, 2015·Chemical Communications : Chem Comm·Yaya DuanJi-Chang Xiao
Jun 15, 2017·Angewandte Chemie·Minsoo JuJennifer M Schomaker
May 15, 2010·The Journal of Organic Chemistry·Alan ArmstrongJames N Scutt
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Aug 31, 2019·The Journal of Organic Chemistry·Shuqi ChenDingqiao Yang

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