Preparation of Silyl Enol Ethers Derived from α-Phenylseleno aldehydes and α-Phenylseleno ketones

Article abstract of DOI:10.1016/0040-4020(95)00532-D

The best experimental conditions for the preparation of trimethylsilyl enol ethers 3 from α-phenylseleno aldehydes 1, compatible with a limited deselenenylation of the substrate, were studied.Starting from α-phenylseleno ketones 2, the enoxysilanes 4, bearing a vinylic PhSe group, are the major products when triethylamine is the base.Trimethylsilyl enol ethers 5 with an allylic PhSe group are also formed beside 4 when LDA or KH are used at lower temperatures.