Stable Aziridinium Salts as Versatile Intermediates: Isolation and Regio- and Stereoselective Ring-Opening and Rearrangement

✍ Scribed by Hyun A. Song; Mamta Dadwal; Yeseul Lee; Emily Mick; Hyun-Soon Chong

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 602 KB
• Volume: 48
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200805244

✦ Synopsis

Abstract

Rock trapping and exploration: Aziridinium bromide salts were discovered serendipitously during bromination of N,N‐dicarboxymethylated β‐amino alcohols. Regiospecific ring‐opening and rearrangement of the isolated, surprisingly stable aziridinium salts produces useful molecules including C‐functionalized oxomorpholines and α,β‐unsaturated amines.magnified image