ChemInform Abstract: Preparation of Cysteinol Derivatives by Highly Regioselective Ring Opening of Nonactivated Chiral Aziridines by Thiols.

✍ Scribed by Jae Hyun Bae; Seong-Ho Shin; Chan Sun Park; Won Koo Lee

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199950198

✦ Synopsis

Preparation of Cysteinol Derivatives by Highly Regioselective Ring Opening of Nonactivated Chiral Aziridines by Thiols. -Ring opening reactions of nonactivated aziridines (I) (12 examples) with thiols, e.g. (II) and (IV), proceed with high regioselectivity and generate chiral cysteinol derivatives (III) and (V) in high yields. The reaction rate of the ring opening reaction increases with the acidity of the thiols, e.g. (IVa) and (IVb). The ring opening products are potentially useful for the synthesis of biologically important compounds. -(BAE,