Issue 32, 2011
From the journal:

Chemical Communications

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

D. Christopher Braddock,*a   Jared S. Marklewa  and  Alexander J. F. Thomasb  

* Corresponding authors

a Department of Chemistry, Imperial College London, London, UK
E-mail: c.braddock@imperial.ac.uk
Fax: +44(0)2075945805
Tel: +44(0)2075945772

b Arrow Therapeutics Ltd, Britannia House, 7 Trinity Street, London SE1 1DB, UK

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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Article information

DOI
https://doi.org/10.1039/C1CC13619D
Article type
Communication
Submitted
17 Jun 2011
Accepted
01 Jul 2011
First published
18 Jul 2011

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

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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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