RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2014; 25(5): 603-607
DOI: 10.1055/s-0033-1340467
DOI: 10.1055/s-0033-1340467
synpacts
Efficient and Stereoselective Nitration of Olefins with AgNO2 and TEMPO
Weitere Informationen
Publikationsverlauf
Received: 08. Oktober 2013
Accepted: 21. November 2013
Publikationsdatum:
13. Januar 2014 (online)
Abstract
Synthetic utility of nitroolefins in fundamental organic synthesis has inspired us to develop a method to access nitroolefins stereoselectively starting from olefins. Silver nitrite along with catalytic TEMPO was found to be the reagent combination of choice. The method enjoys a broad scope and functional-group tolerance while nitroolefins are obtained in high yields with excellent E-selectivity.
-
References
- 1 Huang HB, Jacobsen EN. J. Am. Chem. Soc. 2006; 128: 7170
-
2a Basavaiah D, Reddy BS, Badsara SS. Chem. Rev. 2010; 110: 5447
- 2b Nair DK, Mobin SM, Namboothiri IN. N. Org. Lett. 2012; 14: 4580
- 3a Evans DA, Mito S, Seidel D. J. Am. Chem. Soc. 2007; 129: 11583
- 3b Albrecht L, Dickmeiss G, Acosta FC, Rodriguez-Escrich C, Davis RL, Jørgensen KA. J. Am. Chem. Soc. 2012; 134: 2543
- 4 Fioravanti S, Pellacani L, Tardella PA, Vergari MC. Org. Lett. 2008; 10: 1449
- 5 Jovel I, Prateeptongkum S, Jackstell R, Vogl N, Weckbecker C, Beller M. Adv. Synth. Catal. 2008; 350: 2493
- 6a Tinsley SW. J. Org. Chem. 1961; 26: 4723
- 6b Corey EJ, Estreicher H. J. Am. Chem. Soc. 1978; 100: 6294
- 6c Mukaiyama T, Hata E, Yamada T. Chem. Lett. 1995; 505
- 6d Suzuki H, Mori T. J. Org. Chem. 1997; 62: 6498
- 6e Campos PJ, Garcia B, Rodriguez MA. Tetrahedron Lett. 2000; 41: 979
- 6f Kancharla PK, Reddy YS, Dharuman S, Vankar YD. J. Org. Chem. 2011; 76: 5832
- 7 Manna S, Maity S, Rana S, Agasti S, Maiti D. Org. Lett. 2012; 14: 1736
- 8 Maity S, Manna S, Rana S, Naveen T, Mallick A, Maiti D. J. Am. Chem. Soc. 2013; 135: 3355