Organocatalytic Asymmetric Tandem Michael-Henry Reaction

Significance An organocatalytic asymmetric tandem reaction for the construction of highly functionalized cyclohexane carbaldehydes is described. Chiral α,α-diphenylprolinol silyl ether 1 (10 mol%) mediates a Michael addition of pentane-1,5-dial ( 3 ) to nitroolefins 2 followed by an intra­molecular Henry reaction to give products of type 4 in good yields, diastereoselectivities and excellent enantioselectivities. Two C-C bonds and four stereocenters are generated in the process.