Chiral Lithium Amido Zincates for Enantioselective 1,2-Additions: Auto-assembling Reagents Involving a Fully Recyclable Ligand

Chemistry. 2018 Jul 2;24(37):9238-9242. doi: 10.1002/chem.201802044. Epub 2018 May 29.

Abstract

A methodology consisting in carrying out enantioselective nucleophilic 1,2-additions (ee values up to 97 %) from cheap, easily accessible, and never described before, chiral lithium amido zincates is presented. These multicomponent reactants auto-assemble when mixing, in a 1:1 ratio, a homoleptic diorganozinc (R2 Zn) with a chiral lithium amide (CLA). The latter, obtained after a single reductive amination, plays the role of the chiral inductor and is fully recoverable thanks to a simple acid-base wash, allowing being recycled and re-use without loss of stereochemical information.

Keywords: 1,2 nucleophilic addition; alkylation; chiral lithium amido zincate; organo(bi)metallic; recyclable chiral inductor.