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Synthesis of Selenoaziridines: A Study on Stereochemical Outcomes of the Reaction of Aziridine Radicals and Anions Generated from Iodoaziridines.

ABSTRACT: The synthesis of a new functional group in the form of selenyl-substituted aziridines is described. Selenoaziridines are stereoselectively prepared by functionalization of intact aziridine precursors involving radical and anionic intermediates. Radicals are generated from cis-N-Ts iodoaziridines by activation of the C-I bond using alkoxides as a source of single electrons. These form predominantly trans-substituted selenoaziridines dependent on the size of the diselenide. cis-Aziridinyllithiums generated by Li-I exchange also react with diselenides stereospecifically to form a range of cis-selenoaziridines. Proposals for the stereochemical outcome are presented.

SUBMITTER: Boultwood T

PROVIDER: S-EPMC6648590 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Synthesis of Selenoaziridines: A Study on Stereochemical Outcomes of the Reaction of Aziridine Radicals and Anions Generated from Iodoaziridines.

Boultwood Tom T Bull James A JA

ACS omega 20190110 1

The synthesis of a new functional group in the form of selenyl-substituted aziridines is described. Selenoaziridines are stereoselectively prepared by functionalization of intact aziridine precursors involving radical and anionic intermediates. Radicals are generated from cis-N-Ts iodoaziridines by activation of the C-I bond using alkoxides as a source of single electrons. These form predominantly trans-substituted selenoaziridines dependent on the size of the diselenide. <i ...[more]

PMID: 31459364

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