Enantioselective Organocatalytic Domino Michael-Michael Addition Reactions

Significance

The authors developed an efficient, asymmetric organocatalytic domino Michael-Michael addition reaction of α,β-unsaturated aldehydes 1 with trans-ethyl-4-mercapto-2-butenoate (2) in the presence of (S)-diphenylprolinol TMS ether (3). The reaction worked well with aromatic (bearing neutral, electron-donating or electron-withdrawing groups), heteroaromatic, and aliphatic α,β-unsaturated aldehydes 1 and provided chiral tetrahydrothiophenes 4 containing three stereogenic centers in good to excellent enantio­selectivities and high diastereoselectivities.