Co(Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Esters

Author:

Pugliese Giacomo1,Vaghi Francesco1,Lonardi Giovanni1,Licini Giulia1,Orlandi Manuel1ORCID

Affiliation:

1. Department of Chemical Sciences University of Padova Via Marzolo, 1 35131 Padova Italy

Abstract

AbstractCo‐Salox complexes are suitable catalysts for the reduction of prochiral α,β‐unsaturated esters. These ligands can be prepared in a single step from available and inexpensive materials, thus representing an easily accessible alternative to previously reported Co‐catalysts. NaBH4 is employed as reducing agent in the presence of EtOH as proton source, leading to the stereoselective formation of chiral esters, amides, and nitriles in up to 99 % yield and 96.5 : 3.5 er. The concentration of the reductant counter cation (Na+) and the solvent polarity have been shown to correlate with reactivity and enantioselectivity, suggesting that a relatively complex mechanistic manifold is in place.

Funder

Università degli Studi di Padova

European Commission

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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