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Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides
Nagamalla, Someshwar Mague, Joel T. Sathyamoorthi, Shyam
Nagamalla, Someshwar
Mague, Joel T.
Sathyamoorthi, Shyam
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Abstract
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.
Description
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, Copyright © 2023 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.3c00053.
Date
2023-02-06
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American Chemical Society
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Keywords
Cyclization, Ethers, Mixtures, Ring opening reactions, Substitution reactions
Citation
Nagamalla, S., Mague, J. T., & Sathyamoorthi, S. (2023). Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides. Organic letters, 25(6), 982–986. https://doi.org/10.1021/acs.orglett.3c00053