Oxazolidinone-Promoted, Torquoselective Nazarov Cyclizations

Oxazolidinones are powerful promoters of the Nazarov reaction, enabling the cyclization of conventionally resistant substrates to be achieved under mild conditions. They exert excellent regio- and torquoselective control in both the conventional Nazarov reaction giving cyclopentenones and in the “in...

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Bibliographic Details
Published in:Organic letters 2012-04, Vol.14 (7), p.1732-1735
Main Authors: Kerr, Daniel J, Miletic, Michael, Chaplin, Jason H, White, Jonathan M, Flynn, Bernard L
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Molecular Structure
Oxazolidinones - chemistry
Stereoisomerism
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Summary:Oxazolidinones are powerful promoters of the Nazarov reaction, enabling the cyclization of conventionally resistant substrates to be achieved under mild conditions. They exert excellent regio- and torquoselective control in both the conventional Nazarov reaction giving cyclopentenones and in the “interrupted” Nazarov reaction, giving more highly substituted multistereocenter containing products.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300316a