Enantioselective transformation of alpha,beta-unsaturated ketones using chiral organic catalysts

摘要

Nonmetallic organic catalysts are provided that facilitate the enantioselective reaction of α,β-unsaturated ketones. The catalysts are chiral imidazolidinone compounds having the structure of formula (IIA): or (IIB): or are acid addition salts thereof, wherein, in one preferred embodiment, R1 is C1-C6 alkyl, R2 is phenyl or 2-methylfuryl, R3 and R4 are hydrogen, and R5 is phenyl optionally substituted with 1 or 2 substituents selected from the group consisting of halo, hydroxyl, and C1-C6 alkyl. The chiral imidazolinones are useful in catalyzing a wide variety of reactions, including cycloaddition reactions, Friedel-Crafts alkylation reactions, and Michael additions.