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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

Authors


Cheong, PH More by this author
Blasco Mata, JM More by this author
Stanway, SJ More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Journal:
Journal of the American Chemical Society
Volume:
131
Issue:
5
Pages:
1947-1957
Publication date:
2009-02-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:8a203284-8bde-4f08-b5a6-85e40048666a
Source identifiers:
34561
Local pid:
pubs:34561

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