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Chiral Lithium Amido Zincates for Enantioselective 1,2‐Additions: Auto‐assembling Reagents Involving a Fully Recyclable Ligand
Author(s) -
Rouen Mathieu,
Chaumont Pauline,
BarozzinoConsiglio Gabriella,
Maddaluno Jacques,
HarrisonMarchand Anne
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802044
Subject(s) - enantioselective synthesis , homoleptic , lithium amide , lithium (medication) , reagent , chemistry , amination , combinatorial chemistry , amide , ligand (biochemistry) , reductive amination , nucleophile , base (topology) , organic chemistry , catalysis , mathematics , medicine , mathematical analysis , endocrinology , metal , biochemistry , receptor
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 (R 2 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.