Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines

David Olson, Autumn Maruniak, Sushant Malhotra, Barry M. Trost, J. Du Bois

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Rhodium-catalyzed oxidative cyclization of allylic hydroxylamine-derived sulfamate esters furnishes a novel family of bicyclic aziridines that serve as functional precursors to substituted diamines. Investigations with the N4-Troc form of these heterocycles have led to manifold improvements in reaction performance and scope and have revealed unique differences in the stability and reactivity of such compounds dictated by the choice of N4-protecting group.

Original languageEnglish (US)
Pages (from-to)3336-3339
Number of pages4
JournalOrganic Letters
Volume13
Issue number13
DOIs
StatePublished - Jul 1 2011
Externally publishedYes

Fingerprint

Aziridines
Rhodium
Hydroxylamine
Diamines
Cyclization
diamines
rhodium
esters
Esters
reactivity
routes
synthesis
sulfamic acid

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines. / Olson, David; Maruniak, Autumn; Malhotra, Sushant; Trost, Barry M.; Du Bois, J.

In: Organic Letters, Vol. 13, No. 13, 01.07.2011, p. 3336-3339.

Research output: Contribution to journalArticle

Olson, David ; Maruniak, Autumn ; Malhotra, Sushant ; Trost, Barry M. ; Du Bois, J. / Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines. In: Organic Letters. 2011 ; Vol. 13, No. 13. pp. 3336-3339.
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