Asian Journal of Research in Chemistry
  • Year: 2021
  • Volume: 14
  • Issue: 2

Domino Prins cyclisation for Stereoselective synthesis of Oxygen bridged bicyclic thioethers using Amberlyst-15

  • Author:
  • N. Prudhviraju1,*, R.L. Satyanarayana1, S. Ramesh1, J. Padmavathi1, B. Nagamani1, B. Jagan Mohan Reddy2, B. V. Subba Reddy3
  • Total Page Count: 7
  • Published Online: Jun 24, 2021
  • Page Number: 125 to 131

1B.V. Raju College, Vishnupur, Bhimavaram, West Godavari District, 534202, India.

2Department of Organic Chemistry, Adikavi Nannaya University, Rajahamahendravaram, 533105, India.

3Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, 500007, Hyderabad, India

*Corresponding Author E-mail: prudhvi115@gmail.com

Abstract

A domino reaction has been developed for the synthesis of Oxygen bridged bicyclic thio ethers through the coupling of 4-(2-mercaptoethyl)-1-methylcyclohex-3-en-1-ol with aldehydes in the presence of Amberlyst-15 in dichloromethane at 25°C. This method is a highly diastereoselective affording the corresponding bicyclic thio ethers i.e. (1R,4aR,7R,8aR)-7-methyl-1-(2,4,5-trifluorophenyl)octahydro-4a,7-epoxyisothiochromene in good yields with high selectivity. It is the first report on the synthesis of Oxygen bridged bicyclic thioethers using a domino Prins strategy.

Keywords

Amberlyst-15, Dichloromethane, 4-(2-mercaptoethyl)-1-methylcyclohex-3-en-1-ol, Octahydro- 4a, 7-epoxyisochromenes, Domino Prins