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

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

doi:10.1021/ol302895f

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 journal › Article › peer-review

16 Scopus citations

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 language	English (US)
Pages (from-to)	6174-6177
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	24
DOIs	https://doi.org/10.1021/ol302895f
State	Published - Dec 21 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Roberts, D. Allen

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AB - 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.

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

Abstract

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