Abstract
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.
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