Diastereo- and Enantioselective Iridium Catalyzed Carbonyl (α-Cyclopropyl)allylation via Transfer Hydrogenation

The first examples of diastereo- and enantioselective carbonyl α-(cyclopropyl)allylation are reported. Under the conditions of iridium catalyzed transfer hydrogenation using the chiral precatalyst (R)-Ir-I modified by SEGPHOS, carbonyl α-(cyclopropyl)allylation may be achieved with equal facility from alcohol or aldehyde oxidation levels. This methodology provides a conduit to hitherto inaccessible inaccessible enantiomerically enriched cyclopropane-containing architectures. Alcohol solves problems: Chiral iridium catalysts modified by (R)-SEGPHOS catalyze the transfer hydrogenative coupling of racemic α-cyclopropyl allyl acetate with diverse primary alcohols with good anti-diastereo- and exceptional enantioselectivity. These processes represent the first diastereo- and enantioselective carbonyl (α-cyclopropyl)allylations.