Diastereoselective synthesis of substituted tetrahydrothiopyrans via (3,5)-thionium-ene cyclization reaction

Somasekhar Bondalapati; Paramartha Gogoi; Kiran Indukuri; Anil K Saikia

doi:10.1021/jo2023944

Diastereoselective synthesis of substituted tetrahydrothiopyrans via (3,5)-thionium-ene cyclization reaction

J Org Chem. 2012 Mar 2;77(5):2508-12. doi: 10.1021/jo2023944. Epub 2012 Feb 17.

Authors

Somasekhar Bondalapati¹, Paramartha Gogoi, Kiran Indukuri, Anil K Saikia

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.

PMID: 22316166
DOI: 10.1021/jo2023944

Abstract

Tetrahydrothiopyrans have been efficiently synthesized in good yields with excellent diastereoselectivity from aldehydes and substituted 5-methylhex-4-ene-1-thiol via (3,5)-thionium-ene cyclization reaction mediated by boron trifluoride etherate.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry
Cyclization
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry
Quaternary Ammonium Compounds / chemical synthesis
Quaternary Ammonium Compounds / chemistry*
Stereoisomerism
Sulfhydryl Compounds / chemistry

Substances

Aldehydes
Pyrans
Quaternary Ammonium Compounds
Sulfhydryl Compounds
thionium