Enantioselective Reductive Conjugate Alkenylation of α,β-Unsaturated Ketones and Amides via Nickel Catalysis

Abstract

Chiral nickel complexes promoted enantioselective reductive alkenylation of a range of conjugated enones, using alkenyl bromides, triflates, and tosylates. The neutral condition was compatible with sensitive groups and azaheteroaryl rings. Importantly, alkenyl groups in products can be readily converted to functionalized alkyl groups via iron-catalyzed reductive hydrofunctionalization. Some examples of asymmetric alkenylation of N-enoyl pyrroles and indoles were also included.

Cobalt-Catalyzed Enantioselective Reductive Arylation, Heteroarylation, and Alkenylation of Michael Acceptors via an Elementary Mechanism of 1,4-Addition

“…Our group also disclosed the nickel-catalyzed enantioselective conjugate addition of aryl and alkenyl halides to 2-enones in excellent stereoselectivity (Figure a) . We found that the aryl insertion proceeded via a novel mechanism on nickel complexes, which we called “elementary 1,4-addition” .…”