Brønsted Acid-Catalysed Epoxide Ring-Opening Using Amine Nucleophiles: A Facile Access to β-Amino Alcohols

Chem Asian J. 2022 Jul 15;17(14):e202200379. doi: 10.1002/asia.202200379. Epub 2022 May 23.

Abstract

A mild, efficient, and metal-free synthetic protocol for the synthesis of β-amino alcohols is reported. The reaction proceeds at room temperature with only 0.5 mol % catalyst loading and affords β-amino alcohol derivatives in excellent yield. This protocol is well-tolerated by a wide range of styrene oxide and aniline derivatives. A notably efficacious gram-scale synthesis is also reported with a high TON=842. Further, the Hammett correlation study was also performed to identify the rate-determining step.

Keywords: aniline; metal-free; phenyl oxirane; β-amino alcohols.

MeSH terms

  • Amines*
  • Amino Alcohols*
  • Catalysis
  • Epoxy Compounds
  • Metals

Substances

  • Amines
  • Amino Alcohols
  • Epoxy Compounds
  • Metals