Highly Enantio- and Diastereoselective Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Allyl Ketones

The asymmetric allylic alkylation of Morita–Baylis–Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared.