Journal article

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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APA Style

Robertson, J., Hall, M., & Green, S. (2009). Stereospecific alpha-methallylation of hydroxyaldehydes by silatropic ene cyclisation. TETRAHEDRON, 65(28), 5541–5551.

MLA Style

Robertson, J, et al. “Stereospecific Alpha-Methallylation of Hydroxyaldehydes by Silatropic Ene Cyclisation.” TETRAHEDRON, vol. 65, no. 28, 2009, pp. 5541–51.

Chicago Style

Robertson, J, M Hall, and S Green. 2009. “Stereospecific Alpha-Methallylation of Hydroxyaldehydes by Silatropic Ene Cyclisation.” TETRAHEDRON 65 (28): 5541–51.
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Publisher copy:: 10.1016/j.tet.2009.01.117

Authors

+ Robertson, J More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Hall, M More by this author

Role:: Author

+ Green, S More by this author

Role:: Author

Journal:: TETRAHEDRON More from this journal
Volume:: 65
Issue:: 28
Pages:: 5541-5551
Publication date:: 2009-07-11
DOI:: 10.1016/j.tet.2009.01.117
ISSN:: 0040-4020

Language:: English
Pubs id:: pubs:55215
UUID:: uuid:ecddc4e5-a9d0-47c0-9ecf-cf586b1102fc
Local pid:: pubs:55215
Source identifiers:: 55215
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_ecddc4e5a9d047c09ecfcf586b1102fc

Terms of use

Copyright date:: 2009

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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