Amidines as potent nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
2007; Elsevier BV; Volume: 48; Issue: 34 Linguagem: Inglês
10.1016/j.tetlet.2007.06.112
ISSN1873-3581
AutoresSimon M. Ahmad, D. Christopher Braddock, Gemma Cansell, Stephen A. Hermitage, Joanna M. Redmond, Andrew J. P. White,
Tópico(s)Oxidative Organic Chemistry Reactions
Resumo(±)-iso-Amarine is a potent organocatalyst at 1 mol % loading for both the bromoacetoxylation of alkenes with added acetic acid and bromolactonisation of unsaturated carboxylic acids with stoichiometric NBS as the electrophilic bromine source. A simple bromoamidine with an N–Br bond has been characterised crystallographically for the first time. Asymmetric induction in the bromination reactions with enantiopure amidines was zero.
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