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 | |
| State | Published - Dec 21 2012 |
| Externally published | Yes |
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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 journal › Article
}
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 -