Application of 5-Ethoxymethylfurfural (EMF) for the Production of Cyclopentenones

Abstract

We describe a method for the conversion of 5-ethoxymethylfurfural (EMF) into substituted cyclopentenones in a stereoselective manner through application of the Piancatelli rearrangement. The strategy allows the utilization of biomass-derived C₆-carbohydrates for the production of cyclopentenones, making them a possible platform chemical for the sustainable chemical industry.

Key words

cyclopentenone - 5-ethoxymethylfurfural - 5-hydroxymethylfurfural - Piancatelli rearrangement - biomass valorization

• References

• 1a Schmidts V, Fredersdorf M, Lübken T, Porzel A, Arnold N, Wessjohann L, Thiele CM. J. Nat. Prod. 2013; 76: 839
• 1b Das S, Panda A, Pal S. Carbohydr. Res. 2015; 416: 24
• 1c Ramana GV, Rao BV. Tetrahedron Lett. 2006; 47: 4441
• 1d Mandai H, Omori K, Yamamoto D, Tsumura T, Murota K, Yamamoto S, Mitsudo K, Ibaragi S, Sasaki A, Maeda H, Takashiba S, Suga S. Bioorg. Med. Chem. 2014; 22: 5338
• 1e Lindquist N, Fenical W, Sesin DF, Ireland CM, Duyne GD. V, Forsyth CJ, Clardy J. J. Am. Chem. Soc. 1988; 110: 1308
• 1f Usami Y, Ikura T, Amagata T, Numata A. Tetrahedron: Asymmetry 2000; 11: 3711
• 1g Feng Z, Leutou AS, Yang G, Nenkep VN, Siwe XN, Choi H.-D, Kang J.-S, Son B.-W. Bull. Korean Chem. Soc. 2009; 30: 2345
• 2a Frontier AJ, Collison C. Tetrahedron 2005; 61: 7577
• 2b Pellissier H. Tetrahedron 2005; 61: 6479
• 2c Tius MA. Eur. J. Org. Chem. 2005; 2193
• 2d Vaidya T, Eisenberg R, Frontier AJ. ChemCatChem 2011; 3: 1531
• 2e Wenz DR, Read de Alaniz J. Eur. J. Org. Chem. 2015; 23
• 3a Shibata T. Adv. Synth. Catal. 2006; 348: 2328
• 3b Blanco-Urgoiti J, Añorbe L, Pérez-Serrano L, Domíngueza G, Pérez-Castells J. Chem. Soc. Rev. 2004; 33: 32
• 4 Kalaitzakis D, Triantafyllakis M, Alexopoulou I, Sofiadis M, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2014; 53: 13201

For reviews see:
• 5a Piancatelli G, D’Auria M, D’Onofrio F. Synthesis 1994; 867
• 5b Piancatelli G, Scettri A, Barbadoro S. Tetrahedron Lett. 1976; 3555
• 6a Veits GK, Wenz DR, Read de Alaniz J. Angew. Chem. Int. Ed. 2010; 49: 9484 ; Angew. Chem. 2010, 122, 9674
• 6b Palmer LI, Read de Alaniz J. Angew. Chem. Int. Ed. 2011; 50: 7167 ; Angew. Chem. 2011, 123, 7305
• 6c Palmer LI, Read de Alaniz J. Org. Lett. 2013; 15: 476
• 6d Wenz DR, Read de Alaniz J. Org. Lett. 2013; 15: 3250
• 6e Palmer LI, Veits GK, Read de Alaniz J. Eur. J. Org. Chem. 2013; 6237
• 6f Fisher D, Palmer LI, Cook JE, Davis JE, Read de Alaniz J. Tetrahedron 2014; 70: 4105
• 6g Palmer LI, Read de Alaniz J. Synlett 2014; 25: 8
• 7a Liu J, Shen Q, Yu J, Zhu M, Han J, Wang L. Eur. J. Org. Chem. 2012; 6933
• 7b Reddy BV. S, Narasimhulu G, Lakshumma PS, Reddy YV, Yadav JS. Tetrahedron Lett. 2012; 53: 1776
• 7c Reddy BV. S, Reddy YV, Lakshumma PS, Narasimhulu G, Yadav JS, Sridhar B, Reddy PP, Kunwar AC. RSC Adv. 2012; 2: 10661
• 7d Yin B.-L, Wu Y.-L, Lai J.-Q. Eur. J. Org. Chem. 2009; 2695

For reviews see:
• 8a Van Putten R.-J, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG. Chem. Rev. 2013; 113: 1499
• 8b Hu L, Zhao G, Hao W, Tang X, Sun Y, Lin L, Liu S. RSC Adv. 2012; 2: 11184
• 8c Zakrzewska ME, Bogel-Łukasik E, Bogel-Łukasik R. Chem. Rev. 2011; 111: 397
• 8d Rosatella AA, Simeonov SP, Frade RF. M, Afonso CA. M. Green Chem. 2011; 13: 754
• 9a Roche SP, Aitken DJ. Eur. J. Org. Chem. 2010; 5339
• 9b Arisetti N, Reiser O. Org. Lett. 2015; 17: 94
• 10a Yang Y, Du Z, Huang Y, Lu F, Wang F, Gao J, Xu J. Green Chem. 2013; 15: 1932
• 10b Ulbrich K, Kreitmeier P, Reiser O. Synlett 2010; 2037
• 10c Morgan BS, Hoenner D, Evans P, Roberts SM. Tetrahedron: Asymmetry 2004; 15: 2807
• 10d Ghorpade SR, Bastawade KB, Gokhale DV, Shinde PD, Mahajan VA, Kalkote UR, Ravindranathan T. Tetrahedron: Asymmetry 1999; 10: 4115
• 11a Ohyama J, Kanao R, Esakia A, Satsuma A. Chem. Commun. 2014; 50: 5633
• 11b Ohyama J, Kanao R, Ohira YA, Satsuma A. Green Chem. 2016; 18: 676
• 12a Yang Y, Abu-Omar MM, Hu C. Appl. Energy 2012; 99: 80
• 12b Wang H, Deng T, Wang Y, Qi Y, Hou X, Zhu Y. Bioresour. Technol. 2013; 136: 394
• 12c Wang H, Deng T, Wang Y, Cui X, Qi Y, Mu X, Hou X, Zhu Y. Green Chem. 2013; 15: 2379
• 12d Kim B, Jeong J, Shin S, Lee D, Kim S, Yoon H.-J, Cho JK. ChemSusChem 2010; 3: 1273
• 12e Lew CM, Rajabbeigi N, Tsapatsis M. Ind. Eng. Chem. Res. 2012; 51: 5364
• 13a Mascal M, Nikitin EB. Angew. Chem. Int. Ed. 2008; 47: 7924
• 13b Mascal M, Nikitin EB. ChemSusChem 2009; 2: 859
• 13c Kumari N, Olesen JK, Pedersen CM, Bols M. Eur. J. Org. Chem. 2011; 1266
• 13d Bredihhin A, Mäeorg U, Vares L. Carbohydr. Res. 2013; 375: 63
• 13e Viil I, Bredihhin A, Mäeorg U, Vares L. RSC Adv. 2014; 4: 5689
• 14a Antunes MM, Russo PA, Wiper PV, Veiga JM, Pillinger M, Mafra L, Evtuguin DV, Pinna N, Valente AA. ChemSusChem 2014; 7: 804
• 14b Neves P, Antunes MM, Russo PA, Abrantes JP, Lima S, Fernandes A, Pillinger M, Rocha SM, Ribeiro MF, Valente AA. Green Chem. 2013; 15: 3367
• 14c Lanzafame P, Temi DM, Perathoner S, Centi G, Macario A, Aloise A, Giordano G. Catal. Today 2011; 175: 435
• 14d Alam MI, De S, Dutta S, Saha B. RSC Adv. 2012; 2: 6890
• 14e Balakrishnan M, Sacia ER, Bell AT. Green Chem. 2012; 14: 1626