Vicinal Diamination of Alkenes under Rh-Catalysis

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-10, Vol.136 (39), p.13506-13509
Main Authors: Olson, David E, Su, Justin Y, Roberts, D. Allen, Du Bois, J
Format: Article
Language:English
Subjects:
Alkenes
Alkenes - chemistry
Amination
Catalysis
Communication
Diamines
Diamines - chemical synthesis
Diamines - chemistry
Hot water
Molecular Structure
Organometallic Compounds - chemistry
Pyridines
Rhodium - chemistry
Ring opening
Synthesis
Utilities
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja506532h