Brucine Diol-Catalyzed Enantioselective Morita-Baylis-Hillman Reaction in the Presence of Brucine N-Oxide

Brucine diol (BD) catalyzed asymmetric Morita–Baylis–Hillman (MBH) reaction is observed for the first time. N-oxide (BNO) was found to not have an effective chiral catalyst. Faster rate obtained using unsaturated ester or aromatic aldehydes in presence of BNO. 4-Nitrobenzaldehyde and α,β-unsaturated ketone/ester were converted MBH adduct moderate yields (up 74%) with 70% ee value by this catalytic system. The mechanism BD catalysis probably initiated conjugating vicinal carbonyl group aldehyde through hydrogen bonding. tertiary amine acts as a nucleophile activate vinyl ketone coupling intramolecular carbonylated reaction. Finally, breakdown complex caused formation (a benzyl-allyl alcohol). chirality alcohol likely affected interaction bulky plane BD.