Asymmetric Synthesis of Pentasubstituted Cyclohexanes through Diphenylprolinol Silyl Ether Mediated Domino Michael/Michael Reaction

An asymmetric domino Michael/Michael reaction of alpha,beta-unsaturated aldehydes 1 and alpha-acetyl-beta-substituted-alpha,beta-unsaturated esters 2 catalyzed by diphenylprolinol silyl ether was developed. This is a formal carbo [4+2] cycloaddition reaction affording penta-substituted cyclohexanes having the three continuous chiral centers with excellent diastereo- and enantioselectivity.

Automated summary

The asymmetric domino Michael/Michael reaction catalyzed by diphenylprolinol silyl ether results in the formation of penta-substituted cyclohexanes with three continuous chiral centers, showing excellent diastereo- and enantioselectivity.