Asymmetric Michael Reaction of Malononitrile and α,β-Unsaturated Aldehydes Catalyzed by Diarylprolinol Silyl Ether

An asymmetric Michael reaction of malononitrile and alpha,beta-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether was developed. Michael products were obtained in good yields and with excellent enantioselectivities without the formation of overreaction products. As a malononitrile moiety can be transformed into an alkoxy or amino carbonyl moiety by oxidative transformation, alpha-chiral esters or amides with all-carbon quaternary centers can be synthesized with excellent enantioselectivities.

Automated summary

An asymmetric Michael reaction of malononitrile and alpha,beta-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether was developed. The Michael products were obtained in good yields and with excellent enantioselectivities without the formation of overreaction products. The malononitrile moiety can be transformed into an alkoxy or amino carbonyl moiety by oxidative transformation, allowing the synthesis of alpha-chiral esters or amides with all-carbon quaternary centers and excellent enantioselectivities.