Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides

We describe the development of the first ring opening of epoxides using pendant sulfamates and sulfamides. These reactions are promoted by a base and proceed under mild conditions to afford oxathiazinanes and cyclic sulfamides with excellent diastereoselectivity and regiocontrol. The reactions scale well, and the products serve as synthons for ring-opening reactions.

Automated summary

This paper presents the development of a novel method for the ring opening of epoxides using pendant sulfamates and sulfamides. These reactions, catalyzed by a base, proceed under mild conditions and exhibit excellent diastereoselectivity and regiocontrol in the formation of oxathiazinanes and cyclic sulfamides. The scalability of these reactions is demonstrated, and the resulting products can serve as valuable intermediates for further ring-opening reactions.