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

Lookup NU author(s): Dr Michael HallORCiD

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Abstract

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.

Publication metadata

Author(s): Robertson J, Hall MJ, Green SP

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2009

Volume: 65

Issue: 28

Pages: 5541-5551

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tet.2009.01.117

DOI: 10.1016/j.tet.2009.01.117

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