Abstract
Herein we report the first practical and efficient method for the synthesis of chiral 6-substituted thiomorpholin-3-ones via asymmetric thia-Michael addition reactions between aryl/heteroaryl nitroalkenes and methyl 2-mercaptoacetate by using chiral thiourea catalysts followed by intramolecular reductive cyclization in good yields with selectivities up to 95% ee. The effects of solvent, temperature, substrate concentration, and catalyst loading on asymmetric thia-Michael addition reactions are discussed. The construction of these chiral thiomorpholin-3-ones by this synthetic route would expand upon diversity of the libraries of pharmaceutical interest.
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