Issue 32, 2011

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

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

Supplementary files

Article information

Article type
Communication
Submitted
17 Jun 2011
Accepted
01 Jul 2011
First published
18 Jul 2011

Chem. Commun., 2011,47, 9051-9053

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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