An Organocatalytic Domino Thia-Michael/Aldol Condensation Reaction: Highly Enantioselective Synthesis of Functionalized Dihydrothiophenes

An organocatalytic domino thia-Michael/aldol condensation reaction of a, beta-unsaturated aldehydes with 1, 4-dithiane-2,5-diol catalyzed by chiral diphenylprolinol TMS ether has been developed, which provides a new practical and direct route to chiral dihydrothiophenes with high yields (up to 90%) and excellent enantioselectivities (up to > 99% ee). The catalytic mechanism of the domino reaction was further confirmed through the APCI-MS detection of proposed reaction intermediates.