Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether‐mediated Domino Reaction

Abstract

AbstractBicyclo[2.2.2]octane derivatives possessing a quaternary bridgehead carbon were synthesized with excellent diastereoselectivity in nearly optically pure form by diphenylprolinol silyl ether mediated domino Michael/Michael reaction of α,β‐unsaturated aldehyde and cyclohex‐2‐en‐1‐one bearing an electron‐withdrawing group at the 3‐position. Carbonitrile, alkoxycarbonyl, and sulfonyl substituents were successfully employed as a suitable electron‐withdrawing group at the 3‐position of cyclohex‐2‐en‐1‐one.