Organocatalytic Domino Double Michael Reaction of Ethyl (E)-7-Oxohept-2-enoate and α,β-Unsaturated Aldehydes: Efficient Asymmetric Synthesis of Cyclohexanes with Four Contiguous Stereocenters

Abstract

Organocatalytic domino double Michael reactions of ethyl (E)-7-oxohept-2-enoate and α,β-unsaturated aldehydes provided ethyl 2-(2,4-diformyl-3-phenylcyclohexyl)acetate with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (>99% ee). The adducts were further transformed to octahydro-3H-2-benzopyran-3-ones, octahydroisoquinolin-3(2H)-ones, and decahydro-5H-oxazolo[2,3-a]isoquinolin-5-ones.