Abstract
Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.
| Original language | English |
|---|---|
| Pages (from-to) | 4870-4872 |
| Number of pages | 3 |
| Journal | Organic Letters |
| Volume | 13 |
| Issue number | 18 |
| DOIs | |
| Publication status | Published - 16 Sep 2011 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
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Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles. / Zibinsky, Mikhail; Fokin, Valery V.
In: Organic Letters, Vol. 13, No. 18, 16.09.2011, p. 4870-4872.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles
AU - Zibinsky, Mikhail
AU - Fokin, Valery V.
PY - 2011/9/16
Y1 - 2011/9/16
N2 - Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.
AB - Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.
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UR - http://www.scopus.com/inward/citedby.url?scp=80052765079&partnerID=8YFLogxK
U2 - 10.1021/ol201949h
DO - 10.1021/ol201949h
M3 - Article
C2 - 21848347
AN - SCOPUS:80052765079
VL - 13
SP - 4870
EP - 4872
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 18
ER -