Stereospecific α-(methyl)allylation of hydroxyaldehydes by silatropic ene cyclisation

  1. Lookup NU author(s)
  2. Dr Michael Hall
Author(s)Robertson J, Hall MJ, Green SP
Publication type Article
JournalTetrahedron
Year2009
Volume65
Issue28
Pages5541-5551
ISSN (print)0040-4020
ISSN (electronic)1464-5416
Full text for this publication is not currently held within this repository. Alternative links are provided below where available.
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.
PublisherPergamon
URLhttp://dx.doi.org/10.1016/j.tet.2009.01.117
DOI10.1016/j.tet.2009.01.117
Actions    Link to this publication