Organic Chemistry Portal

Abstracts

Search:

Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides

Chuan Wang and Hisashi Yamamoto*

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States, Email: yamamotouchicago.edu

C. Wang, H. Yamamoto, J. Am. Chem. Soc., 2014, 136, 6888-6891.

DOI: 10.1021/ja5029809



see article for more reactions

Abstract

A catalytic, highly C3-selective, stereosepecific ring-opening reaction of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides is efficiently promoted by W-salts. The developed method was applicable to various epoxides with diverse N- and O-nucleophiles affording the products in good to excellent yields (up to 95%) and generally with high regioselectivities (C3:C2 up to >99:1).

see article for more examples



Key Words

β-amino alcohols


ID: J48-Y2014