Tetrahedron

Stereospecific α-methallylation of hydroxyaldehydes by silatropic ene cyclisation

J Robertson, MJ Hall, SP Green

文献索引：Robertson, Jeremy; Hall, Michael J.; Green, Stuart P. Tetrahedron, 2009 , vol. 65, # 28 p. 5541 - 5551

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被引用次数: 5

摘要

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 ...