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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 (free Supporting Information)



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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).

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Key Words

β-amino alcohols


ID: J48-Y2014