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. 2023 Nov 17;88(22):15989-16006.
doi: 10.1021/acs.joc.3c01731. Epub 2023 Oct 30.

Ring Opening of Aziridines by Pendant Sulfamates Allows for Regioselective and Stereospecific Preparation of Vicinal Diamines

Someshwar Nagamalla  1 , Annu Anna Thomas  1 , Appasaheb K Nirpal  1 , Joel T Mague  2 , Shyam Sathyamoorthi  1
Affiliations

Ring Opening of Aziridines by Pendant Sulfamates Allows for Regioselective and Stereospecific Preparation of Vicinal Diamines

Someshwar Nagamalla et al. J Org Chem. .

Abstract

The ring opening of aziridines by pendant sulfamates is a viable strategy for the rapid preparation of vicinal diamines. Our reaction is compatible with both disubstituted cis- and trans-aziridines; unsubstituted, N-alkyl, and N-aryl sulfamates engage effectively. In all cases examined, the cyclization reaction is perfectly regioselective and stereospecific. Once activated, the product oxathiazinane heterocycles can be ring opened with a diverse range of nucleophiles.

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Figures

Scheme 1.
Scheme 1.
Current strategies to access vicinal diamines inspire our own efforts.
Scheme 2.
Scheme 2.
Representative preparations of aziridine sulfamate substrates.
Scheme 3.
Scheme 3.
Structure-reactivity relationship with various sulfamate esters.
Scheme 4.
Scheme 4.
Structure-reactivity relationship with various aziridine N-substituents.
Scheme 5.
Scheme 5.
Substrate scope.
Scheme 6.
Scheme 6.
Cyclization scales well both cis- and trans-aziridine sulfamate substrates.
Scheme 7.
Scheme 7.
Product oxathiazinane heterocycles are amenable to further functionalization.
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