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

Authors

  • Haizhen Jiang,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China, Fax: +86-21-66133380
    Search for more papers by this author
  • Shijie Yuan,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China, Fax: +86-21-66133380
    Search for more papers by this author
  • Wen Wan,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China, Fax: +86-21-66133380
    2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
    Search for more papers by this author
  • Kun Yang,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China, Fax: +86-21-66133380
    Search for more papers by this author
  • Hongmei Deng,

    1. Instrumental Analysis & Research Center, Shanghai University, 99 Shangda Road, Shanghai 200444, China
    Search for more papers by this author
  • Jian Hao

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China, Fax: +86-21-66133380
    2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
    Search for more papers by this author

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.

Ancillary