1365552-15-3Relevant academic research and scientific papers
Synthesis of silyloxy dienes by silylene transfer to divinyl ketones: Application to the asymmetric synthesis of substituted cyclohexanes
Ventocilla, Christian C.,Woerpel
, p. 3277 - 3283 (2012/05/19)
Silver-catalyzed silylene transfer to divinyl ketones provided 2-silyloxy-1,3-dienes with control of stereochemistry and regioselectivity. The products participated in Diels-Alder reactions with electron-deficient alkenes and imines to form six-membered-ring products diastereoselectively. Cycloaddition reactions with alkenes bearing chiral auxiliaries provided access to chiral, nonracemic cyclohexenes. The methodology, therefore, represents a synthesis of diastereomerically and enantiomerically pure products in a single flask. The highly substituted cyclohexene products could be functionalized stereoselectively to provide cyclohexanols after oxidation of the carbon-silicon bond.
