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. 2023 Feb 17;25(6):982-986.
doi: 10.1021/acs.orglett.3c00053. Epub 2023 Feb 6.

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

Someshwar Nagamalla  1 , Joel T Mague  2 , Shyam Sathyamoorthi  1
Affiliations

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

Someshwar Nagamalla et al. Org Lett. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1.
Scheme 1.
Previous Efforts with Aminolysis of Epoxides Inspire Our Tethered Ring-Opening Approach
Scheme 2.
Scheme 2.
Synthesis of Epoxide Substrates
Scheme 3.
Scheme 3.
Structure–Reactivity Relationship with Various Sulfamate Esters aNumbers in parenthesis indicate (substrate number, product number). Note: only relative stereochemistry is depicted.
Scheme 4.
Scheme 4.
Substrate Scope with Sulfamates and Sulfamides aReaction conditions: Bu4NOH·30H2O (1 equiv), CF3-toluene/H2O, 23 °C, 24–48 h. bSubstrate number, product number. Note: only relative stereochemistry is depicted.
Scheme 5.
Scheme 5.
(A) Interesting and (B) Problematic Substrates
Scheme 6.
Scheme 6.
(A) Ring Opening Scales Successfully and (B) Some Fun with the Product
See this image and copyright information in PMC

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