Amidines as potent nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes

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• 作者：Simon M. Ahmad ; D. Christopher Braddock ; Gemma Cansell ; Stephen A. Hermitage ; Joanna M. Redmond ; Andrew J.P. White
• 关键词：Electrophilic bromination ; Alkenes ; Organocatalysis ; Amidine
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：20 August 2007
• 卷：48
• 期：34
• 页码：5948-5952
• 文件大小：175 K

摘要

(±)-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.