Asymmetric Cyclopentannelation. Chiral Auxiliary on the Allene

An enantioselective variant of the synthesis of cross-conjugated cyclopentenones, based on d-glucose-derived chiral auxiliaries, is described. Minor modification of the method makes it applicable to the preparation of both enantiomeric series of products. Both enantiomers of the key intermediate in...

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Bibliographic Details
Published in:Organic letters 2000-08, Vol.2 (16), p.2447-2450
Main Authors: Harrington, Paul E, Tius, Marcus A
Format: Article
Language:English
Subjects:
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Indicators and Reagents
Models, Molecular
Molecular Conformation
Stereoisomerism
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Summary:An enantioselective variant of the synthesis of cross-conjugated cyclopentenones, based on d-glucose-derived chiral auxiliaries, is described. Minor modification of the method makes it applicable to the preparation of both enantiomeric series of products. Both enantiomers of the key intermediate in our roseophilin synthesis have been prepared.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0001362