Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

Thibault E. Schmid (1) , Sammy Drissi-Amraoui (2) , Christophe Crévisy (1) , Olivier Baslé (1) , Marc Mauduit (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier

The copper-catalyzed asymmetric conjugate addition (ACA) of nucleophiles onto polyenic Michael acceptors represents an attractive and powerful methodology for the synthesis of relevant chiral molecules, as it enables in a straightforward manner the sequential generation of two or more stereogenic centers. In the last decade, various chiral copper-based catalysts were evaluated in combination with different nucleophiles and Michael acceptors, and have unambiguously demonstrated their usefulness in the control of the regio- and enantioselectivity of the addition. The aim of this review is to report recent breakthroughs achieved in this challenging field

Keywords: conjugate additions; electron-deficient alkenes; enantioselective catalysis; extended Michael acceptors; organometallic nucleophiles; sequential addition

Domains: Chemical Sciences

Thibault E. Schmid, Sammy Drissi-Amraoui, Christophe Crévisy, Olivier Baslé, Marc Mauduit. Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors. Beilstein Journal of Organic Chemistry, 2015, 11, pp.2418--2434. ⟨10.3762/bjoc.11.263⟩. ⟨hal-01254825⟩