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 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Olson, D., Roberts, D. A., & Du Bois, J. (2012). Synthesis of differentially substituted 1,2-diamines through advances in C-H amination technology. Organic Letters, 14(24), 6174-6177. https://doi.org/10.1021/ol302895f