Reaction of Acylsilanes with α-Sulfinyl Carbanions; Regioselective Formation of Silyl Enol Ethers

摘要

α-Silyl alkoxides are interesting and useful species in synthetic organic chemistry, because of the specific migration behavior of silyl group on them. We have previously reported that reaction of acylsilanes with sulfonium ylides proceeded to give the corresponding silyl enol ethers or β-ketosilanes via α-silyl alkoxide intermediates, and the product's ratio can be controlled by manipulating the reaction conditions. In this context, we were interested in the migratory behavior of silyl group on α-silyl alkoxides derived from the reaction of acylsilanes 1 with α-sulfinyl carbanions 2 as the compounds related to sulfonium ylides. In this paper, we report the generation of α-silyl alkoxides derived from the reaction of acylsilanes with α-sulfinyl carbanions and the following reaction behavior.