866007-57-0Relevant articles and documents
Stereospecific α-methallylation of hydroxyaldehydes by silatropic ene cyclisation
Robertson, Jeremy,Hall, Michael J.,Green, Stuart P.
experimental part, p. 5541 - 5551 (2009/12/09)
We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotylsilyl)oxy substituent. The transformations are best described mechanistically as intramolecular silatropic ene reactions based on stereoselectivity, kinetic and computed transition state data. The overall process constitutes a stereospecific (meth)allylation of α-hydroxyaldehydes, under neutral conditions, in which the hydroxyl protecting group is also the (meth)allylating agent.