Diphenylprolinol Silyl Ether Catalysis in an Asymmetric Formal Carbo [3 + 3] Cycloaddition Reaction via a Domino Michael/Knoevenagel Condensation

Abstract

Diphenylprolinol silyl ether was found to catalyze the formal carbo [3 + 3] cycloaddition reaction through the domino reaction via the Michael reaction, followed by Knoevenagel condensation of the alpha,beta-unsaturated aldehyde and dimethyl 3-oxopentanedioate, affording substituted cyclohexenone derivatives with excellent enantioselectivity.