Abstract
A facile, one-pot synthesis of allylic thioesters starting fromBaylis-Hillman (BH) bromides and N-thioaroylmorpholines isdescribed. The synthesis is performed in a silica gel-watersystem without any additional catalyst or co-catalyst. The reactionpathway involves selective S-alkylation of N-thioaroylmorpholinesvia nucleophilic displacement (S N 2) with BH bromides,followed by hydrolysis to afford the corresponding thioesters. Thepresent synthetic protocol avoids the application of malodoroussulfur compounds of limited accessibility such as thiols, and thioacidsand their salts as reactants.
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