Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles

Org Lett. 2017 Sep 15;19(18):4826-4829. doi: 10.1021/acs.orglett.7b02264. Epub 2017 Sep 1.

Abstract

A nickel-mediated asymmetric allylic alkylation reaction between imidazole-modified ketones and nitroallylic acetates is presented. This reaction is catalyzed by a simple chiral diamine-nickel catalyst under mild conditions and leads to a series of novel enantioenriched α-allylic adducts in moderate to good yields with excellent enantioselectivities. Furthermore, transformation of the allylic adducts could smoothly lead to chiral γ-nitro-esters containing three continuous stereocenters in good yields.

Publication types

  • Research Support, Non-U.S. Gov't