Lookup NU author(s): Dr Michael Hall
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We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotyl-silyl)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.
Author(s): Robertson J, Hall MJ, Green SP
Publication type: Article
ISSN (print): 0040-4020
ISSN (electronic): 1464-5416
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