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. 2016 Mar 24;55(14):4587-90.
doi: 10.1002/anie.201600597. Epub 2016 Mar 4.

Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents

Rik Oost  1 , Antonio Misale  1 , Nuno Maulide  2
Affiliations

Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents

Rik Oost et al. Angew Chem Int Ed Engl. .

Abstract

The first enantioconvergent palladium-catalyzed Fukuyama cross-coupling of racemic benzylic organozinc reagents with thioesters has been developed. The reaction furnishes enantioenriched acyclic α-disubstituted ketone products in good yields and high enantioselectivities. A broad substrate scope is achieved under mild reaction conditions to prevent racemization of the potentially labile tertiary stereocenters.

Keywords: cross-coupling; enantioselectivity; ligand effects; palladium; zinc.

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