Synthesis of differentially substituted 1,2-diamines through advances in C-H amination technology

David Olson, D. Allen Roberts, J. Du Bois

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A general, high yielding method for the synthesis of 1,2-diamine derivatives is described that capitalizes on selective, rhodium-catalyzed C-H insertion of hydroxylamine-based sulfamate esters. The resulting Troc-protected oxathiadiazinane heterocycles are easily modified and can be reduced under the mild action of NaI to afford differentially substituted diamine products. This technology offers a number of salient improvements over related C-H and π-bond amination tactics for diamine synthesis.

Original languageEnglish (US)
Pages (from-to)6174-6177
Number of pages4
JournalOrganic Letters
Volume14
Issue number24
DOIs
StatePublished - Dec 21 2012
Externally publishedYes

Fingerprint

Amination
Diamines
diamines
Technology
synthesis
tactics
Rhodium
Hydroxylamine
rhodium
esters
insertion
Esters
Derivatives
products

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of differentially substituted 1,2-diamines through advances in C-H amination technology. / Olson, David; Roberts, D. Allen; Du Bois, J.

In: Organic Letters, Vol. 14, No. 24, 21.12.2012, p. 6174-6177.

Research output: Contribution to journalArticle

Olson, David ; Roberts, D. Allen ; Du Bois, J. / Synthesis of differentially substituted 1,2-diamines through advances in C-H amination technology. In: Organic Letters. 2012 ; Vol. 14, No. 24. pp. 6174-6177.
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