An efficient and rapid chalcogenide-Morita-Baylis-Hillman process promoted by TBDMSOTf and a thiolane

Abstract

The ability of the combination of sulfide/TBDMSOTf to promote a chalcogenide-Morita-Baylis-Hillman reaction is reported. The original Michael-Mukaiyama-retroaldol sequence took place and furnished the MBH adducts from the corresponding enones and acetals. This one step process could be performed smoothly at low temperatures (-20 to -50 °C) and is rapidly completed within a few hours. © 2006 Elsevier Ltd. All rights reserved.