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Issue 32, 2011
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Enantiospecific bromonium ion generation and intramolecular capture: a model system for asymmetric bromonium ion-induced polyene cyclisations

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Abstract

Scalemic bromonium ions generated enantiospecifically by the action of catalytic triflic acid on scalemic regioisomeric bromohydrin derivatives are trapped intramolecularly, enantiospecifically and regioselectively to give bicyclic brominated carbocycles in excellent yield and high enantiomeric excess. This enantiospecific pathway is not significantly perturbed by the addition of a trisubstituted alkene.

Graphical abstract: Enantiospecific bromonium ion generation and intramolecular capture: a model system for asymmetric bromonium ion-induced polyene cyclisations

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Supplementary files

Article information


Submitted
17 Jun 2011
Accepted
01 Jul 2011
First published
18 Jul 2011

Chem. Commun., 2011,47, 9051-9053
Article type
Communication

Enantiospecific bromonium ion generation and intramolecular capture: a model system for asymmetric bromonium ion-induced polyene cyclisations

D. C. Braddock, J. S. Marklew and A. J. F. Thomas, Chem. Commun., 2011, 47, 9051
DOI: 10.1039/C1CC13619D

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