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

14 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

Access to Document

10.1021/ol302895f

Fingerprint Dive into the research topics of 'Synthesis of differentially substituted 1,2-diamines through advances in C-H amination technology'. Together they form a unique fingerprint.

Cite this

@article{a99d5e69426c4669a137fb9a22a3db67,

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

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.",

author = "David Olson and Roberts, {D. Allen} and {Du Bois}, J.",

year = "2012",

month = dec,

day = "21",

doi = "10.1021/ol302895f",

language = "English (US)",

volume = "14",

pages = "6174--6177",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Synthesis of differentially substituted 1,2-diamines through advances in C-H amination technology

AU - Olson, David

AU - Roberts, D. Allen

AU - Du Bois, J.

PY - 2012/12/21

Y1 - 2012/12/21

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84871549452&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84871549452&partnerID=8YFLogxK

U2 - 10.1021/ol302895f

DO - 10.1021/ol302895f

M3 - Article

C2 - 23227976

AN - SCOPUS:84871549452

VL - 14

SP - 6174

EP - 6177

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 24

ER -