Regioselective and Enantioselective Cu(II)-Catalyzed 1,4-Conjugate Addition of Diethylzinc Reagent to Nitrodienes

Abstract

The regioselective and enantioselective Cu(II)-catalyzed 1,4-conjugate addition of diethylzinc reagent to nitrodienes is described. With 0.25 mol % of Cu(OAc) 2 and chiral amidophosphine ligand L3, the 1,4-addition products were produced with a complete regioselectivity, high yields (81−98%), and excellent enantioselectivities (87−97% ee) in a short reaction time.

Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines

“…Chiral cyclohexane-based N , P -ligands L1–L15 were prepared according to the literature procedure . Isatin-derived ketimines were synthesized by following the literature procedure …”

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

“…Figure 2. Catalysts for asymmetric diethylzinc addition to aldehydes.Enantioselective copper(II)-promoted 1,4-conjugate addition of Et 2 Zn to nitrodienes 106 was reported by Wu et al[97]. The corresponding 1,4-adducts 107 were obtained in 81-98% yield and with 87-97% ee when a chiral amidophosphine ligand 108 was applied (Scheme 35)[97].…”