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Diels-Alder exo selectivity in terminal-substituted dienes and dienophiles: experimental discoveries and computational explanations.

Abstract:

The Diels-Alder reactions of a series of silyloxydienes and silylated dienes with acyclic alpha,beta-unsaturated ketones and N-acyloxazolidinones have been investigated. The endo/exo stereochemical outcome is strongly influenced by the substitution pattern of the reactants. High exo selectivity was observed when the termini of the diene and the dienophile involved in the shorter of the forming bonds were both substituted, while the normal endo preference was found otherwise. The exo-selective...

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Publication status:
Published

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Publisher copy:
10.1021/ja8079548

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Journal:
Journal of the American Chemical Society
Volume:
131
Issue:
5
Pages:
1947-1957
Publication date:
2009-02-01
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Source identifiers:
34561
Language:
English
Keywords:
Pubs id:
pubs:34561
UUID:
uuid:8a203284-8bde-4f08-b5a6-85e40048666a
Local pid:
pubs:34561
Deposit date:
2012-12-19

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