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

Rouen, Mathieu;Chaumont, Pauline;Barozzino Consiglio, Gabriella;Maddaluno, Jacques;Harrison-Marchand, Anne
(2018) Chemistry: A European Journal — Vol. 24, n° 37, p. 9238-9242 (2018)

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Abstract
A methodology consisting in carrying out enantioselective nucleophilic 1,2-additions (ees 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 (R2Zn) 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.
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Rouen, M., Chaumont, P., Barozzino Consiglio, G., Maddaluno, J., & Harrison-Marchand, A. (2018). Chiral Lithium Amido Zincates for Enantioselective 1,2-Additions: Auto-assembling Reagents Involving a Fully Recyclable Ligand. Chemistry: A European Journal, 24(37), 9238-9242. https://doi.org/10.1002/chem.201802044 (Original work published 2018)