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A facile stereoselective synthesis of (Z)- and (E)-allyl sulfides has been accomplished from Morita-Baylis-Hillman acetates in one-pot by treatment with benzene thiol in the presence of catalytic amounts of 15% aqueous NaOH and TBAI in DMSO at room temperature. The method has been applied for the synthesis of (Z)-3-(4-methoxybenzylidene)thiochroman-4-one, a potent antifungal compound.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

A Mild and Efficient Stereoselective Synthesis of (Z)- and (E)-Allyl Sulfides and Potent Antifungal Agent, (Z)-3-(4-Methoxybenzylidene)thiochroman-4-one from Morita-Baylis-Hillman Acetates