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

09 January 2023, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We describe the development of the first ring-opening of epoxides using pendant sulfamates and sulfamides. These reactions are promoted by 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.

Supplementary materials

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Version History

Jan 09, 2023 Version 1

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-2sbfs
D O I: 10.26434/chemrxiv-2023-2sbfs [opens in a new tab]

Funding

National Institutes of Health
R35GM142499

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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