Benzamidoxime-Mediated Crotylation of Aldehydes using Potassium (Z) and (E)-Crotyltrifluoroborates
DOI:
https://doi.org/10.29356/jmcs.v62i1.577Keywords:
Crotylation reaction, homoallylic alcohols, benzamidoxime, potassium organotrifluoroboratesAbstract
A highly diastereoselective protocol for the crotylation reaction of aldehydes using potassium (Z) and (E)-crotytrifluoroborates was developed. Benzamidoxime was employed as a renewable catalyst, which was easily recovered through a simple extraction process. This method proved to be simple, fast, regio- and chemoselective for different aldehydes. The corresponding homoallylic alcohols were obtained in good to excellent yields without the need of further purification.Downloads
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Altiti, A. S.; Bachan, S.; Mootoo, D. R. Org. Lett. 2016, 18, 4654-4657. DOI: https://doi.org/10.1021/acs.orglett.6b02284
Liang, T.; Zhang, W.; Chen, T.-Y.; Nguyen, K. D.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 13066-13071. DOI: https://doi.org/10.1021/jacs.5b08019
Nowrouzi, F.; Thadani, A. N.; Batey, R. A. Org. Lett. 2009, 11, 2631-2634. DOI: https://doi.org/10.1021/ol900599q
O’Hora, P. O.; Incerti-Pradilhos, C. A.; Kabeshov, M. A.; Shipilovskikh, S. A.; Rubtsov, A. E.; Elsegood, M. R. J.; Malkov, A. V. Chem. Eur. J. 2015, 21, 4551-4555. DOI: https://doi.org/10.1002/chem.201500176
Itoh, T.; Montgomery, P.; Recio, A.; Krische, M. J. Org. Lett. 2014, 16, 820-823. DOI: https://doi.org/10.1021/ol403566w
Thadani, A. N.; Batey, R. A. Tetrahedron Lett. 2003, 44, 8051-8055. DOI: https://doi.org/10.1016/j.tetlet.2003.09.053
de Fátima, A.; Pilli, R. A. Tetrahedron Lett. 2003, 44, 8721-8724. DOI: https://doi.org/10.1016/j.tetlet.2003.09.122
Fujii, K.; Maki, K.;Kanai, M.;Shibazaki, M. Org. Lett. 2003, 5, 733-736. DOI: https://doi.org/10.1021/ol027528o
Fargeas, V.; Zammattio, F.; Chrétien, J.-M.; Bertrand, M.-J.; Paris, M.; Quintard, J.-P. Eur. J. Org. Chem. 2008, 1681-1688. DOI: https://doi.org/10.1002/ejoc.200701183
de Fátima A.; Robello, G. L.; Pilli, R. A. Quim. Nova. 2006, 29, 1009-1026. DOI: https://doi.org/10.1590/S0100-40422006000500023
Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc. 1980, 23, 102, 7107-7109. DOI: https://doi.org/10.1021/ja00543a040
Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763-2794. DOI: https://doi.org/10.1021/cr020050h
Kim, I. S.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514-2520. DOI: https://doi.org/10.1021/ja808857w
Souza, T. R. C. L. Métodos Verdes de Alilação de Aldeídos com Organotrifluoroboratos. Universidade Federal de Pernambuco, Brazil, 2015.
Roy, U. K.; Roy, S. Tetrahedron Lett. 2007, 48, 7177-7180. DOI: https://doi.org/10.1016/j.tetlet.2007.07.201
McCubbin, J. A.; Maddess, M. L.; Lautens, M. Synlett. 2011, 19, 2857-2861. DOI: https://doi.org/10.1055/s-0031-1289565
Kim, H.; Ho, S.; Leighton, J. L. J. Am. Chem. Soc. 2011, 133, 6517-6520. DOI: https://doi.org/10.1021/ja200712f
Nowrouzi, F.; Batey, R. A. Angew. Chem. In. Ed. 2013, 52, 892-895. DOI: https://doi.org/10.1002/anie.201207978
Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron. 2007, 63, 3623-3658. DOI: https://doi.org/10.1016/j.tet.2007.01.061
Lennox, A. J. J.; Lloyd-Jones, G. C. Angew. Chem. Int. Ed. 2012, 51, 9385-9388. DOI: https://doi.org/10.1002/anie.201203930
Janetzko, J; Batey, R. A. J. Org. Chem. 2014, 79, 7415-7424. DOI: https://doi.org/10.1021/jo501134d
Cella, R.; Venturoso, R. C.; Stefani, A. H. Tetrahedron Lett. 2008, 49, 16-19. DOI: https://doi.org/10.1016/j.tetlet.2007.11.031
Barros, C. J. P.; de Souza, Z. C.; Freitas, J. J. R.; da Silva, P. B. N.; Militão, G. C. G.; Silva, T. G.; Freitas, J. C. R.; Freitas Filho, J. R. J. Am. Chem. Soc. 2014, 59, 2359-2362. DOI: https://doi.org/10.4067/S0717-97072014000100024
Freitas, J. J. R.; Freitas, J. C. F.; da Silva, L. P.; de Freitas, J. R.; Kimura, G. Y. V.; Srivastava, R. M. Tetrahedron Lett. 2007, 48, 6195-6198. DOI: https://doi.org/10.1016/j.tetlet.2007.06.116
Tang, D.; Li, X.- L.; Guo, X.; Wu, P.; Li, J.-H.; Wang, K.; Jing, H.- W. Tetrahedron 2014, 70, 4038-4042. DOI: https://doi.org/10.1016/j.tet.2014.04.054
Wu, Z.-C.; Huang, Y.; Lu, Y.-N.; Tao, T.-X.; Zhang, Z. Suzuki Cat. Comm. 2012, 29, 158-161. DOI: https://doi.org/10.1016/j.catcom.2012.09.034
Veisi, H.; Sedrpoushan, A.; Maleki, B.; Hekmati, M.; Heidari, M.; Hemmati, S. Appl. Org. Chem. 2015, 29, 834-839 DOI: https://doi.org/10.1002/aoc.3390
Freitas Filho, J. R.; da Silva, R. L.; da Silva, E. E.; Santos, J. A. M.; de Freitas, J. J. R.; Freitas, J. C. R. Rev. Virtual Quím. 2015, 6, 2549-2596. DOI: https://doi.org/10.5935/1984-6835.20150153
Metwally, S. S.; Ayoub, R. R.; Aly, H. F. Sep. Sci. Techn. 2013, 48, 1830-1840. DOI: https://doi.org/10.1080/01496395.2012.755697
Liu, X.; Chen, H.; Wang, C. H.; Qu, R. J.; Ji, C. N.; Sun, C. M.; Xu, Q. Pol. Adv. Techn. 2011, 22, 2032-2038. DOI: https://doi.org/10.1002/pat.1714
Zhao, Y.; Li, J.; Zhao, L.; Zhang, S.; Huang, Y.; Wu, X.; Wang, X. Chem. Eng. J. 2014, 235, 275-283. DOI: https://doi.org/10.1016/j.cej.2013.09.034
Coskun, R.; Dilci, Y.; J. J. Mac. Sci. part a-pure Appl. Chem. 2014, 51, 767-782. DOI: https://doi.org/10.1080/10601325.2014.937122
Andrade, D.; Freitas Filho, F. R.; Freitas, J. C. R. Quim. Nova 2016,39, 1225-1235.
Freitas, J. J. R.; Couto, T. R.; Cavalcanti, I. H.; Freitas, J. C. R.; Oliveira, R. A.; Menezes, P. H. Ultrason. Sonochem. 2014, 21, 1609-1614. DOI: https://doi.org/10.1016/j.ultsonch.2014.04.001
Silva, J. F.; Lima, J. A. C.; Freitas, J. J. R.; Freitas, L. P. S. R.; Menezes, P. H.; Freitas, J. C. R. Lett. Org. Chem. 2016, 13, 49-57. DOI: https://doi.org/10.2174/1570178612666150928195725
Batey, R. A.; Thadani, A. N.; Smil, D. V. Tetrahedron Lett. 1999, 40, 4289-4292. DOI: https://doi.org/10.1016/S0040-4039(99)00774-1
Freitas, J. C. R.; Oliveira, C. K.; Cunha, E. C.; Malvestiti, I.; Alves Jr., S.; Longo, R. L.; Menezes, P. H. Tetrahedron Lett. 2013, 54, 1558-1561. DOI: https://doi.org/10.1016/j.tetlet.2013.01.035
Barros, C. J. P.; de Freitas, J. J. R.; de Oliveira, R. N.; Freitas Filho, J. R. J. J. Chil. Chem. Soc. 2011, 56, 721-722. DOI: https://doi.org/10.4067/S0717-97072011000200022
Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer-Verlag: Berlin, 1995. DOI: https://doi.org/10.1007/978-3-642-79709-5
Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1981, 103, 1969-1975. DOI: https://doi.org/10.1021/ja00398a016
Le Serre, S.; Guillemin, J. C. Organomet. 1997, 16, 5844-5848. DOI: https://doi.org/10.1021/om9706471
Perrin, D. D.; Amarego, W. L. F. Purification of Laboratory Chemicals. Boston: Oxford, 1997.
Wang, X.; Dong, S.; Feng, D.; Chen, Y.; Ma, M.; Hu, W. Tetrahedron 2017, 73, 2255-2266. DOI: https://doi.org/10.1016/j.tet.2017.03.006
Suzuki, I.; Esumi, N.; Yasuda, M. Asian J. Org. Chem. 2016, 5, 179-182. DOI: https://doi.org/10.1002/ajoc.201500475
Goswami, D.; Koli, M. R.; Chatterjee, S.; Chattopadhyay, S.; Sharma, A. Org. Biomol. Chem. 2017, 15, 3566-3774 DOI: https://doi.org/10.1039/C7OB00626H
Akira, Y.; Aoki, T.; Arai, T. Synlett. 2006, 2071-2074. DOI: https://doi.org/10.1055/s-2006-948198
Zbieg, J. R.; Yamaguchi, E.; Mclnturff, E.; Krische, M. J. Science. 2012, 336, 324-327. DOI: https://doi.org/10.1126/science.1219274
Masuyama, Y.; Saeki, K.; Horiguchi, S.; Kurusu, Y. Synlett. 2001, 1802-1804. DOI: https://doi.org/10.1055/s-2001-18102
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