Significance of Povarov Reaction in Organic synthesis: An overview

Authors

  • Shivaji Jadhav
  • Rashmi Pathrikar
  • Sumit Shejul

DOI:

https://doi.org/10.46243/jst.2022.v7.i01.pp73-90

Keywords:

Povarov reaction, multicomponent one-pot synthesis, cycloaddition, molecular diversity, organic synthesis.

Abstract

:The Povarov reaction has enabled and shaped the art and science of organic synthesis over the last few decades to an extent that has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent Pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Povarov cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. Selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of organic synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.

References

L. S. Povarov, B. M. Mikhailov, Izv. Akad. Nauk SSR, Ser. Khim., 1963,953

L. S. Povarov, V. I. Grigos, B. M. Mikhailov, Izv. Akad. Nauk SSR, Ser. Khim.,1963, 2039

L. S. Povarov, Russian Chem. Rev., 1967, 36, 656

L. S. Povarov, B. M. Mikhailov, Izv. Akad. Nauk SSR, Ser. Khim., 1964, 2221

V. I. Grigos, L. S. Povarov, B. M. Mikhailov, Izv. Akad. Nauk SSR, Ser. Khim., 1965,2163

V. V. Kouznetsov, Tetrahedron. 2009, 65, 2721

V. Sridharan, P. A. Suryavanshi, J. C.Menendez, Chem. Rev., 20114, 111, 7157

V. Luchini, M. Prato, G. Scorrano, M. Stivanel, G. Valle, J. Chem. Sec.-Perkin Trans., 1992, 2, 259

T. Joh, H. Hagihara, Tetrahedron Lett., 1967, 8, 4199

S. Kobayashi, H. Ishitani, S. Nagayama, Synthesis., 1995, 1195. Published by: Longman Publishers www.jst.org.in P a g e 89 | 18

M. Xia, Y. Lu, Syn.Lett., 2005,2357

R. Suresh, S.Muthusubramanian, R. Senthilkumaran, G. Manickam, J. Org. Chem.,2012, 77, 1468

S. Wang, Y. L. Zhao, W. Zhang, Q. Liu, J. Org. Chem., 2007, 72, 4985

(a) K. De, J. Legros, B. Crousse, D. Bonnet-Delpon, J. Org. Chem., 2009, 74, 6260; (b) K. De, J. Legros, B. Crousse, D. Bonnet-Delpon, Tetrahedron, 200864, 10497; (c) K. De, J. Legros, B. Crousse, J, Crousse, B. Chandrasekaran, D. Bonnet-Delpon, Org. Biomol. Chem.2011, 9, 347

F. Palacios, C. Alonso, A. Arrieta, F. P. Cossio, J. Ezpeleta, M. Fuertes, G. Rubiates, Eur.J. Org. Chem., 2010, 2091

L. R. Domingo, M. J. Aurella, J. A. Saez, S. M. Makelleche, RSC Adv., 2014, 4

(a) M. Terada, Y. Matsumoto, Y. Nakamura, K. Mikami, Chem.Commun,.1997, 281; (b) S. Kobayashi, H. Ishitani, S. Nagayama, Chem. Lett., 1995, 423

E. Wada, H. Yasuoka, S. Kanemasa, Chem. Lett., 1994, 1637

(a) G. Babu, P. T. Perumal, Tetrahedron Lett, 1997, 38, 5025; (b) G. Babu, P. T. Perumal, Tetrahedron, 1998, 54, 1627

G. Sundarajan, N. Prabhakaran, B. Varghase, Org. Lett., 2001, 1973

Liu Hue, D. Guillaume, Pascal Retailleau, Zhu Jieping, J. A. M. Chem. Soc.2009, 000, 131, 4598

U. Pindur, M. H. Kim, Tetrahedron Lett., 1998, 29, 3927

Review: G. Adais.; S. Mukherjee, B. List., Alderichmica Aeta., 2008, 41, 31

S. Hoffman, A. M. Seayad, B. List., Chem. Int. Ed., 2005, 44, 7424

Giulia Bergonzini, LiciaGramigna, M. Andre, F. Mariafrancesca, LueaBemardi, Alfredo Ricchi., Chem.,Comm., 2010, 46, 327

(a) A. R. Katritzky, S. Rachwal, B. Rachwal, Tetrahedron, 1996, 52,15031; (b) R. Perez-Ruiz, L. R. Domingo, M. C. Jimenez, M. A. Miranda, Org. Lett., 2011, 13, 5116; (c) V. V. Kouznetsov, Tetrahedron, 65, 2721 (2009).; (d) P. Buonora, J. C. Olsen, T. Oh, Tetrahedron,2001, 57, 6099

F. Fadel, S. L. Titouani, M. Soufiaoui, H. Ajamay, A. Mazzah, Tetrahedron Lett., 2004, 45 5905

J. F. Kervin Jr., S. Danishefsky, Tetrahedron Lett., 1982, 23, 3739

Y. Zhang, X. Dai, W. Wang, Zhang, Tetrahedron Lett., 2011, 52, 6122

K. Makino, Y. Henmi, M. Terasawa, O. Hara, Y. Hamada, Tetrahedron Lett., 2005, 46,555

(a) G. Babu, P. T. Perumal, Tetrahedron Lett., 1997, 38, 5025; (b) J. Zhang, C. J. Li, J. Org. Chem., 2002, 67, 3969

(a) B. Das, M. R. Reedy, V. S. Reddy, R. Ramu, Chem. Lett., 2004, 33,1526; (b) M. Mahesh, C. V. Reddy, K. S. Reddy, P. V. K. Raju, V.V. N. Reddy, Synth. Commun., 2004, 34,4089

(a) P. A. Grieco, A. Bahsas, Tetrahedron Lett. 1988, 29, 5855; (b) J. M. Mellor, G. D. Merriman, P. Riviere, Tetrahedron,1991, 32, 7103

[33]D. L. Boger, Oxford., 1991, 451

T. Akiyama, J. Takaya, H. Kagoshima, Tetrahedron Lett., 1999, 40, 7831

(a) S. Kobayashi, M. Araki, H. Ishitani, S. Nagayama, I. Hachiya, Synlett, 1995, 3, 233; (b) S. Luo, L. Zhu, A. Taludar, G. Zhang, X. Mi, J. Chjeng, P. Wang, Org. Chem., 2005, 2, 546; (c) K. Turhan, E. Pelit, Z. Turgut, Synth.Commun., 2009, 39, 1729

(a) V. Sridharan, C. Avendano, J. C. Menendez, Tetrahedron,2007, 63,673; (b) G. Savitha, P. T. Perumal, Tetrahedron Lett., 2006,47, 3589

E. Rajanarendar, M. N. Reddy, K. G. Reddy, S. R. Krishna, Tetrahedron Lett., 2012, 53, 2909

K. Nagaiah, D. Sreenu, R. Srinivasa Rao, G. Vashishta, J. S. Yadav, Tetrahedron Lett., 2006, 47, 4409

J. S. Yadav, B. V. S. Reddy, K. Sadashiv, P. S. R. Reddy, Tetrahedron Lett., 2002, 43,3853

EmelPetil, Zuhal Turgut, Ultrasonochemistry, 2014, 21, 1600

Guillaume Dagousset, Jieping Zhu, Geraldine Masson. J. Am. Chem. Soc., 2011, 133, 14804

Chih-Hau Chem, S. Gorakh, Yellol, Po-Tsung Lin, and Chung-Ming Sun, Organic letters., 2011, 13 (19)5120

X. M. Feng, X. H. Liu, Nova Science, New York, 2011, 1

H. Ishitani, S. Kobayashi, Tetrahedron Lett., 1996,37, 7357. Published by: Longman Publishers www.jst.org.in P a g e 90 | 18 a) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc., 2006, 128, 13070; b) H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. P. Zhu, J. Am. Chem. Soc., 2009, 131, 4598; (c) G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi, A. Ricci, Chem. Commun., 2010, 46, 327, 406; d) G. Dickmeiss, K. L. Jensen, D. Worgull, P. T. Franke, K. A. Jorgensen, Angew. Chem. 2011, 123, 1618

MingshengXie, Xieaohua Liu, Yin Zhu, Xiaohu Zhao, Yong Xia, Lili Lin, Xiaomi ng Feng, Chem. Eur. J. 2011, 17, 13800

Xiaodong Jia, Chang Qing, Congde Hua, Fangfanf Peng, Xicun Wang, Tetrahedron letters, 2012, 53, 7140

C. N. Ganguly, Sumanta Chandra, Tetrahedron letters, 2014, 55, 1564

R. B. Carmindo, Luiz Claudio, Celia Regina Alvares Maltha, Sergio Antonio Fernandes, Tetrahedron Letters,2015, 56, 662

M. J. Rai, S. L. Jadhav, and M. N. Farooqui, Orbital: Electron. J. Chem. 2016,8 (3), 149

Zhang, Y.Q., Zhang, Y.P., Zhang, Y.X., Li, Z.Y. and Ye, L.W., Cell Reports Physical Science, 2021, 2(6), p.100448

Gao, Q., Liu, S., Wu, X., Zhang, J. and Wu, A., The Journal of Organic Chemistry, 2015, 80(11), pp.5984- 5991

Published

2022-05-21

How to Cite

Jadhav, S., Pathrikar, R., & Sumit Shejul. (2022). Significance of Povarov Reaction in Organic synthesis: An overview. Journal of Science & Technology , 7(Special Issue 1), 73–90. https://doi.org/10.46243/jst.2022.v7.i01.pp73-90