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Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols.

Abstract:
A variety of routes are described for the synthesis of a-silyloxy aldehydes in which the silicon atom bears a prenyl side chain. These compounds are shown to undergo stereoselective carbonyl ene cyclisation under mildly Lewis acidic conditions and the derived silacycles are cleaved to afford single diastereomers of functionalised triols.
Publication status:
Published

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Publisher copy:
10.1039/b306922m

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry
Volume:
1
Issue:
21
Pages:
3758-3767
Publication date:
2003-11-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Language:
English
Pubs id:
pubs:55234
UUID:
uuid:c718e6aa-56c0-47b3-9bbf-b23e8d71c6c0
Local pid:
pubs:55234
Source identifiers:
55234
Deposit date:
2012-12-19

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