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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Facile Synthesis of Electron-deficient Epoxides Adjacent to Ester and Cyanide Groups

Author(s): Sujata V. Bhat*, Mayur Uttekar and Manisha O. Gupta

Volume 21, Issue 1, 2024

Published on: 10 October, 2023

Page: [7 - 11] Pages: 5

DOI: 10.2174/1570178620666230705123035

Price: $65

Abstract

The addition of camphor and oxone® during the epoxidation led to the synthesis of seven novel epoxides. Since the tri-substituted double bond of -cyano-cinnamates has been epoxidized, the reaction is easier to carry out and cleaner, producing a high yield of epoxides. Several molecules with industrial applications will result from the selective ring opening of epoxides.

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[1]
Bonini, C.; Lupattelli, P. ARKIVOC, 2008, 2008(8), 150-182.
[http://dx.doi.org/10.3998/ark.5550190.0009.814]
[2]
Bégué, D.; Bonnet, J.; Delpon, P.; Kornilov, A. Org. Synth., 1998, 75, 153.
[http://dx.doi.org/10.15227/orgsyn.075.0153]
[3]
Mello, R.; Alcalde-Aragonés, A.; González Núñez, M.E.; Asensio, G. J. Org. Chem., 2012, 77(15), 6409-6413.
[http://dx.doi.org/10.1021/jo300533b] [PMID: 22812696]
[4]
Lopez-Pedrosa, J.M.; Pitts, M.R.; Roberts, S.M.; Saminathan, S.; Whittall, J. Tetrahedron Lett., 2004, 45(26), 5073-5075.
[http://dx.doi.org/10.1016/j.tetlet.2004.04.190]
[5]
Geller, T.; Gerlach, A.; Krüger, C.M.; Militzer, H.C. Tetrahedron Lett., 2004, 45(26), 5065-5067.
[http://dx.doi.org/10.1016/j.tetlet.2004.04.188]
[6]
Fraile, J.M.; García, J.I.; Marco, D.; Mayoral, J.A. Appl. Catal. A Gen., 2001, 207(1-2), 239-246.
[http://dx.doi.org/10.1016/S0926-860X(00)00626-8]
[7]
Yamu, X.; Haixin, L.; Xiaoli, D. J. Chem. Res., 2013, 2013, 531-534.
[8]
Ghosh, A.K.; Kim, J.H. Org. Lett., 2004, 6(16), 2725-2728.
[http://dx.doi.org/10.1021/ol0490835] [PMID: 15281754]
[9]
Aggarwal, V.K.; Hynd, G.; Picoul, W.; Vasse, J.L. J. Am. Chem. Soc., 2002, 124(34), 9964-9965.
[http://dx.doi.org/10.1021/ja0272540] [PMID: 12188641]
[10]
Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem. Int. Ed., 2005, 44(28), 4389-4391.
[http://dx.doi.org/10.1002/anie.200500938]
[11]
Faveri, G.D.; Ilyashenko, G.; Watkinson, M. Chem. Soc. Rev., 2011, 40, 1722-1760.
[http://dx.doi.org/10.1039/C0CS00077A] [PMID: 21079863]
[12]
Shi, Y. Acc. Chem. Res., 2004, 37(8), 488-496.
[http://dx.doi.org/10.1021/ar030063x] [PMID: 15311947]
[13]
Nieto, N.; Munslow, I.J.; Fernández-Pérez, H.; Vidal-Ferran, A. Synlett, 2008, 2856-2858.
[14]
Wang, B.; Wong, O.A.; Zhao, M.X.; Shi, Y. J. Org. Chem., 2008, 73(24), 9539-9543.
[http://dx.doi.org/10.1021/jo801576k] [PMID: 18850744]
[15]
Burke, C.P.; Shi, Y. J. Org. Chem., 2007, 72(11), 4093-4097.
[http://dx.doi.org/10.1021/jo070205r] [PMID: 17458998]
[16]
Mirata, M.A.; Wüst, M.; Mosandl, A.; Schrader, J. J. Agric. Food Chem., 2008, 56(9), 3287-3296.
[http://dx.doi.org/10.1021/jf800099h] [PMID: 18426215]
[17]
Lee, W.D.; Chiu, C.C.; Hsu, H.L.; Chen, K. Tetrahedron, 2004, 60(31), 6657-6664.
[http://dx.doi.org/10.1016/j.tet.2004.05.095]
[18]
Gaikwad, R.D.; Kabiraj, S.S.; Bhat, S.V. Flavour Fragrance J., 2016, 31(5), 350-355.
[http://dx.doi.org/10.1002/ffj.3322]
[19]
Ahmat, Y.M.; Madadi, S.; Charbonneau, L.; Kaliaguine, S. Catalysts, 2021, 11, 847-864.
[http://dx.doi.org/10.3390/catal11070847]
[20]
Mangaonkar, S.R.; Singh, F.V. Synthesis, 2019, 51.
[21]
Mitra, A.K.; De, A.; Karchaudhuri, N. Synth. Commun., 1999, 29(16), 2731-2739.
[http://dx.doi.org/10.1080/00397919908086438]
[22]
Wan, J.P.; Jing, Y.; Liu, Y.; Sheng, S. RSC Advances, 2014, 4(109), 63997-64000.
[http://dx.doi.org/10.1039/C4RA13826K]
[23]
Panja, S.K.; Dwivedi, N.; Saha, S. RSC Advances, 2015, 5(80), 65526-65531.
[http://dx.doi.org/10.1039/C5RA09036A]

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