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Vicinal diamination of alkenes under Rh-catalysis.

ABSTRACT: The synthesis of 1,2-diamines has been achieved through a single-step, tandem sequence involving Rh-catalyzed aziridination followed by NaI-promoted rearrangement to an isomeric cyclic sulfamide. Facile ring opening of these products in hot water and pyridine affords differentially protected vicinal diamines. Demonstration of the utility of this method for the syntheses of (±)-enduracididine and (±)-allo-enduracididine is highlighted.

SUBMITTER: Olson DE

PROVIDER: S-EPMC4183635 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Vicinal diamination of alkenes under Rh-catalysis.

Olson David E DE Su Justin Y JY Roberts D Allen DA Du Bois J J

Journal of the American Chemical Society 20140918 39

The synthesis of 1,2-diamines has been achieved through a single-step, tandem sequence involving Rh-catalyzed aziridination followed by NaI-promoted rearrangement to an isomeric cyclic sulfamide. Facile ring opening of these products in hot water and pyridine affords differentially protected vicinal diamines. Demonstration of the utility of this method for the syntheses of (±)-enduracididine and (±)-allo-enduracididine is highlighted. ...[more]

PMID: 25233140

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