Pd-Catalyzed Carbonylative Conjugate Addition of Dialkylzinc Reagents to Unsaturated Carbonyls

Catalytic enantioselective conjugate addition of dialkylzinc reagents to N-substituted-2,3-dehydro-4-piperidones.

The first, highly enantioselective, copper/phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents to N-substituted 2,3-dehydro-4-piperidones is described.

Copper-catalyzed Enantioselective Conjugate Addition Reactions of Organozinc Reagents

Conjugate addition (1,4-addition) of carbon nucleophiles to a; b-unsaturated compounds is one of the most important carbon–carbon bond-forming strategies in synthetic organic chemistry [1]. The versatility of the conjugate addition is mainly due to the large variety of nucleophiles (organometallic reagents, Michael donors, other carbanions) and acceptors (a; b-unsaturated aldehydes, ketones, ni...

Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones.

A highly regioselective and enantioselective copper-catalyzed 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones was developed. The 1,4-addition products were obtained regioselectively in high yields with up to 98% ee.

Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: preparation of air-stable and catalytically active Cu-peptide complexes.

Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones.

It is no longer necessary to use dialkylzinc reagents to obtain enantioselectivities >95% in the copper-catalyzed asymmetric conjugate addition of organometallic compounds to cyclic enones. We now report how this can be accomplished by using inexpensive and readily available Grignard reagents. Screening of bidentate ligands provided outstanding results with copper complexes of commercially avai...