Vicinal diamination of alkenes under Rh-catalysis

David Olson, Justin Y. Su, D. Allen Roberts, J. Du Bois

Research output: Contribution to journalArticle

58 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)13506-13509
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number39
DOIs
StatePublished - Oct 1 2014
Externally publishedYes

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Diamines
Alkenes
Catalysis
Olefins
Pyridine
Demonstrations
Water
L-allo-enduracididine
pyridine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Vicinal diamination of alkenes under Rh-catalysis. / Olson, David; Su, Justin Y.; Roberts, D. Allen; Du Bois, J.

In: Journal of the American Chemical Society, Vol. 136, No. 39, 01.10.2014, p. 13506-13509.

Research output: Contribution to journalArticle

Olson, David ; Su, Justin Y. ; Roberts, D. Allen ; Du Bois, J. / Vicinal diamination of alkenes under Rh-catalysis. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 39. pp. 13506-13509.
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