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Stereospecific alpha-methallylation of hydroxyaldehydes by silatropic ene cyclisation

Abstract:
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. © 2009 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Publisher copy:
10.1016/j.tet.2009.01.117

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
TETRAHEDRON
Volume:
65
Issue:
28
Pages:
5541-5551
Publication date:
2009-07-11
DOI:
ISSN:
0040-4020
URN:
uuid:ecddc4e5-a9d0-47c0-9ecf-cf586b1102fc
Source identifiers:
55215
Local pid:
pubs:55215
Language:
English

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