Bromotriphenylphosphonium Salt Promoted Tandem One-Pot Cyclization to Optically Active 2-Aryl-1,3-oxazolines

✍ Scribed by Haizhen Jiang; Shijie Yuan; Wen Wan; Kun Yang; Hongmei Deng; Jian Hao

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 726 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201000162

✦ Synopsis

Abstract

Optically active 2‐aryl‐1,3‐oxazolines, such as aromaticcarbocycles, heterocycle‐binding 4‐benzyl (or phenyl)‐1,3‐oxazolines and their 5‐benzyl (or phenyl)‐1,3‐oxazoline isomers were successfully prepared through a bromotriphenylphosphonium salt promoted aziridine ring formation and ring opening sequential process involving tandem one‐pot cyclization of chiral 2‐amino‐3‐phenylpropanol or 2‐amino‐2‐phenylethanol with various aromatic acids in toluene at 90 °C in moderate to excellent yields. The mechanism of this tandem process was also substantiated experimentally.