This report describes the development of a chiral Brønsted acid-catalyzed asymmetric MoritaBaylis À Hillman (MBH) reaction of cyclohexenone with aldehydes. During the course of our studies on chiral Lewis acid-promoted MBH reactions, we discovered that chiral binaphthol-derived Brønsted acids serve as promoters of the asymmetric MBH reaction. We propose that the phosphonium enolate of cyclohexenone is stabilized via hydrogen-bonding with the binaphthol-derived Brønsted acid, creating a chiral nucleophile. A practical and efficient set of conditions was developed using stoichiometric PEt 3 as the nucleophilic promoter and catalytic amounts of a binaphthol-derived Brønsted acid to effect the reaction of cyclohexenone with various aliphatic and aromatic aldehydes in good yields and enantiomeric excesses (up to 96% ee).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.