An Enantiospecific Polyene Cyclization Initiated by an Enantiomerically Pure Bromonium Ion

An Enantiospecific Polyene Cyclization Initiated by an Enantiomerically Pure Bromonium Ion

ABSTRACT Dimethylaluminum triflate‐mediated activation of tetrafluorobenzoates of enantiomerically pure bromohydrins results in enantiospecific polyene cyclizations. The initiation of cyclization by enantiomerically pure bromonium ions and subsequent propagation is not subject to catastrophic erosio...

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Veröffentlicht in:Chirality (New York, N.Y.) N.Y.), 2013-11, Vol.25 (11), p.692-700
Hauptverfasser: Braddock, D. Christopher, Marklew, Jared S., Foote, Kevin M., White, Andrew J. P.
Format: Artikel
Sprache:eng
Schlagworte:
Activation
Alcohols - chemistry
bromonium ion
Chirality
Cyclization
enantiospecific
Erosion
polyene cyclization
Polyenes - chemistry
Purity
Stereoisomerism
Substrate Specificity
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Zusammenfassung:ABSTRACT Dimethylaluminum triflate‐mediated activation of tetrafluorobenzoates of enantiomerically pure bromohydrins results in enantiospecific polyene cyclizations. The initiation of cyclization by enantiomerically pure bromonium ions and subsequent propagation is not subject to catastrophic erosion of enantiomeric purity by any intramolecular or intermolecular bromonium ion‐to‐alkene transfer. Chirality 25:692–700, 2013. © 2013 Wiley Periodicals, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22194