Highly Regioselective C(3) Opening of an Aromatic 2,3-Epoxy Alcohol with Sodium Phenoxides or Thiophenoxides (=Benzenethiolates) Supported by β-Cyclodextrin in Water

✍ Scribed by Mendu Narender; Majjigapu Somi Reddy; Yadavalli Venkata Durga Nageswar; Kakulapati Rama Rao

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: German
• Weight: 63 KB
• Volume: 90
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200790109

✦ Synopsis

Abstract

A simple and mild procedure was developed for the first time for the C(3)‐selective ring opening of an aromatic 2,3‐epoxy alcohol, i.e., of trans‐3‐phenyloxirane‐2‐methanol (1), with sodium phenoxides or thiophenoxides (=benzenethiolates) 2 supported by β‐cyclodextrin in H~2~O at 50° to afford the corresponding 3‐(aryloxy)‐ or 3‐(arylthio)propane1,2‐diols 3 in excellent yields (Scheme, Table).