Efficient and Stereoselective Nitration of Olefins with AgNO2 and TEMPO

Soham Maity; Togati Naveen; Upendra Sharma; Debabrata Maiti

doi:10.1055/s-0033-1340467

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(5): 603-607
DOI: 10.1055/s-0033-1340467

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Efficient and Stereoselective Nitration of Olefins with AgNO₂ and TEMPO

Soham Maity

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India eMail: dmaiti@chem.iitb.ac.in

,

Togati Naveen

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India eMail: dmaiti@chem.iitb.ac.in

,

Upendra Sharma

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India eMail: dmaiti@chem.iitb.ac.in

,

Debabrata Maiti*

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India eMail: dmaiti@chem.iitb.ac.in

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Abstract

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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.

Key words

nitroolefin - stereoselective - olefin - nitration - high yields

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Referenzen

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