Transition Metal Catalyzed Isomerization Reaction of Allylic Alcohols

doi:10.6023/cjoc201509030

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 258-273.DOI: 10.6023/cjoc201509030 Previous Articles Next Articles

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过渡金属催化烯丙醇异构化反应的研究进展

钟业辛^a, 任凯^b, 谢小敏^b, 张兆国^a,b

a 上海应用技术学院化学与环境工程学院上海 201418;
b 上海交通大学化学化工学院上海 200240

收稿日期:2015-09-24 修回日期:2015-10-23 发布日期:2015-11-03
通讯作者: 任凯, 张兆国 E-mail:kairenhb@sjtu.edu.cn;zhaoguo@sjtu.edu.cn
基金资助:
国家自然科学基金(No. 21472124)资助项目

Transition Metal Catalyzed Isomerization Reaction of Allylic Alcohols

Zhong Yexin^a, Ren Kai^b, Xie Xiaomin^b, Zhang Zhaoguo^a,b

a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2015-09-24 Revised:2015-10-23 Published:2015-11-03
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21472124).

Carbonyl compounds are key synthetic intermediates in the fields of medicine, pesticide, perfumes and cosmetics. In recent years, transition metal catalyzed isomerization of allylic alcohols to synthesize various carbonyl compounds has drawn much attention and been explored extensively, due to their high atomic economy and unique superiority. The recent development of the isomerization reactions of allylic alcohols catalyzed by various transition metals is summarized.

Key words: allylic alcohols, transition metal, isomerization reaction, carbonyl compounds, asymmetric isomerization reaction , tandem reaction

Cite this article

Zhong Yexin, Ren Kai, Xie Xiaomin, Zhang Zhaoguo. Transition Metal Catalyzed Isomerization Reaction of Allylic Alcohols[J]. Chin. J. Org. Chem., 2016, 36(2): 258-273.

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[1] (a) Yanovskaya, L. A.; Shakhidayatov, K. Russ. Chem. Rev. 1970, 39, 859. (b) Uma, R. C.; Crévisy; Grée, R. Chem. Rev. 2003, 103, 27. (c) van der Drift, R. C.; Bouwman, E.; Drent, E. J. Organoment. Chem. 2002, 650, 1. (d) Manzini, C.; Poater, A.; Nelson, D. J.; Cavallo, L.; Nolan, S. P. Chem. Sci. 2014, 5, 180. (e) Lorenzo-Luis, P.; Romerosa, A.; Serrano-Ruiz, M. ACS Catal. 2012, 2, 1079.
[2] Delaby, R. Compt. Rend. 1926, 182, 140.
[3] Emerson, G. F.; Pettit, R. J. Am. Chem. Soc. 1962, 84, 4591.
[4] Strauss, J. U.; Ford, P. W. Tetrahedron Lett. 1975, 33, 2917.
[5] Branchadell, V.; Crévisy, C.; Grée, R. Chem.-Eur. J. 2004, 10, 5795.
[6] Strohmeier, W.; Weigelt, L. J. Organomet. Chem. 1975, 86, C17.
[7] Crabtree, R. H.; Felkin, H.; Morris, G. E. J. Organomet. Chem. 1977, 141, 205.
[8] Mantilli, L.; Mazet, C. Chimia 2009, 63, 35.
[9] Sato, S. H.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1985, 26, 4229.
[10] Bergens, S. H.; Bosnich, B. J. Am. Chem. Soc. 1991, 113, 958.
[11] de Bellefon, C.; Tanchoux, N.; Caravieilhes, S.; Grenouillet, P.; Hessel, V. Angew. Chem., Int. Ed. 2000, 39, 3442.
[12] Knight, D. A.; Schull, T. L. Synth. Commun. 2003, 33, 827.
[13] Ahlsten, N.; Lundberg, H.; Martín-Mature, B. Green Chem. 2010, 12, 1628.
[14] Chin, C. S.; Lee, S. Y.; Park, J.; Kim, S. J. Am. Chem. Soc. 1988, 110, 8244.
[15] Uma, R.; Davies, M. K.; Crévisy, C.; Grée, R. Eur. J. Org. Chem. 2001, 3141.
[16] Trost, B. M.; Kulawiec, R. J. J. Am. Chem. Soc. 1993, 115, 2027.
[17] Sasson, Y.; Zoran, A.; Blum, J. J. Mol. Catal. 1979, 6, 289.
[18] Dedieu, M.; Pascal, Y.-L. J. Mol. Catal. 1980, 9, 59
[19] Krompiec, S.; Suwinski, J.; Grobelny, R. J. Mol. Catal. 1994, 89, 303.
[20] Stunnenberg, F.; Niele, F. G. M.; Drent, E. Inorg. Chim. Acta. 1994, 222, 225.
[21] Markó, I. E.; Gautier, A.; Tsukazaki, M.; Llobet, A.; Plantalech Mir, E.; Urch, C. J.; Brown, S. M. Angew. Chem., Int. Ed. 1999, 38, 1960.
[22] Alper, H.; Hachem, K. J. Org. Chem. 1980, 45, 2269.
[23] Trost, B. M.; Kuliawec, R. J. Tetrahedron Lett. 1991, 32, 3039.
[24] Bäckvall, J.-E.; Andreasson, U. Tetrahedron Lett. 1993, 34, 5459.
[25] Martín-Mature, B.; Bogar, K.; Edin, M.; Kaynak, F. B.; Bäckvall, J. E. Chem.-Eur. J. 2005, 11, 5832.
[26] Ito, M.; Kitahara, S.; Ikariya, T. J. Am. Chem. Soc. 2005, 127, 6172.
[27] Kechaou-Perrot, M.; Vendier, L.; Bastin, S.; Sotiropoulos, J.-M.; Miqueu, K.; Menéndez-Rodríguez, L.; Crochet, P.; Cadierno, V.; Igau, A. Organometallics 2014, 33, 6294
[28] (a) Cadierno, V.; Garca-Garrido, S. E.; Gimeno, J.; Varela-Álvarez, A.; Sordo, J. A. J. Am. Chem. Soc. 2006, 128, 1360. (b) García-Garrido, S. E.; Gimeno, J.; Suárez, F. J. Organometallics 2011, 30, 2893.
[29] da Costa, A. P.; Mata, J. A.; Royo, B.; Peris, E. Organometallics. 2010, 29, 1832.
[30] Azua, A.; Sanz, S.; Peris, E. Organometallics 2010, 29, 3661.
[31] Díez, J.; Gimeno, J.; Ledós, A.; Suáez, F, J.; Vicent, C. ACS Catal. 2012, 2, 2087.
[32] Kraus, M. Collect. Czech. Chem. Commun. 1972, 37, 460.
[33] Sadeghmoghaddam, E.; Gu, H.; Shon, Y.-S. ACS Catal. 2012, 2, 1838.
[34] Larionov, E.; Lin, L.-Q.; Guénée, L.; Mazet, C. J. Am. Chem. Soc. 2014, 136, 16882.
[35] Goetz, R. W.; Orchin, M. J. Am. Chem. Soc. 1963, 85, 1549.
[36] Corain, B. Gazz. Chim. Ital. 1972, 102, 687.
[37] Corain, B.; Puosi, G. J. Catal. 1973, 30, 403.
[38] Bricout, H.; Monflier, E.; Carpentier, J. F.; Mortreux, A. Eur. J. Inorg. Chem. 1998, 1998, 1739.
[39] Deeming, A. J.; Hasso, S. J. Organomet. Chem. 1976, 114, 313.
[40] Batuecas, M.; Esteruelas, M. A.; Garcia Yebra, C.; Onate, E. Organometallics 2010, 29, 2166.
[41] Tatsumi, T.; Hashimoto, K.; Tominaga, H.; Mizuta, Y.; Hata, K.; Hidai, M.; Uchida, Y. J. Organomet. Chem. 1983, 252, 105.
[42] Botteghi, C.; Giacomelli, G. Gazz. Chim. Ital. 1976, 106, 1131.
[43] Otsuka, S.; Tani, K. Synthesis 1991, 665.
[44] Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
[45] Mantilli, L.; Gerard, D.; Torche, S.; Besnard, C.; Mazet, C. Angew. Chem., Int. Ed. 2009, 48, 5143.
[46] Li, J. Q.; Peters, B.; Andersson, P. G. Chem.-Eur. J. 2011, 17, 11143.
[47] Bizet, V.; Pannecoucke, X.; Renaud, J. L.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 6467.
[48] Wu, R.; Beauchamps, M. G.; Laquidara, J. M.; Sowa, Jr, J. R. Angew. Chem., Int. Ed. 2012, 52, 2106.
[49] Arai, N.; Sato, K.; Azuma, K.; Ohkuma, T. Angew. Chem., Int. Ed. 2013, 52, 7500.
[50] Li, H,-H.; Mazet, C. J. Am. Chem. Soc. 2015, 137, 10720.
[51] Ohkuba, K.; Ohgushi, T.; Kusaga, T.; Yoshinaga, K. Inorg. Nucl. Chem. Lett. 1977, 13, 631
[52] Kitamura, M.; Manabe, K.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4719
[53] Fernández-Zúmel, M. A.; Lastra-Barreina, B.; Scheele, M.; Diez, J.; Crochet, P.; Gimeno, J. Dalton Trans. 2010, 39, 7780.
[54] Corkum, E. G.; Kalapugama, S.; Hass, M. J.; Bergens, S. H. RSC Adv. 2012, 2, 3473.
[55] Ren, K.; Zhang, L.; Hu, B.; Zhao, M.-M.; Tu, Y.-H.; Xie, X.-M.; Zhang, T.-Y.; Zhang, Z.-G. ChemCatChem 2013, 5, 1317
[56] Crévisy, C.; Wietrich, M.; Le Boulaire, V.; Uma, R.; Grée, R. Tetrahedron Lett. 2001, 42, 395.
[57] (a)Wang, M.; Li, C.-J. Tetrahedron Lett. 2002, 43, 3589. (b) Yang, X.-F.; Wang, M.; Varma, R. S.; Li, C.-J. Org. Lett. 2003, 5, 657.
[58] Cuperly, D.; Petrignet, J.; Crévisy, C.; Grée, R. Chem.-Eur. J. 2006, 12, 3261.
[59] Bartoszewicz, A.; Livendahl, M.; Martín-Mature, B. Chem.-Eur. J. 2008, 14, 10547.
[60] Mizuno, A.; Kusama, H.; Iwasawa, N. Chem.-Eur. J. 2010, 16, 8248.
[61] Bartoszewicz, A.; Martín-Matute, B. Org. Lett. 2009, 11, 1749.
[62] Ahlsten, N.; Bartoszewicz, A.; Agrawal, S.; Martín-Matute, B. Synthesis 2011, 2600.
[63] Ahlsten, N.; Bermejo, G. A.; Martín-Matute, B. Angew. Chem., Int. Ed. 2013, 52, 6273.
[64] Gómez, A, B.; Erbing, E.; Batuecas, M.; Vázquez-Romero, A.; Martín-Matute, B. Chem.-Eur. J. 2014, 20, 10703.
[65] Vazquez-Romero, A.; Bermejo, G. A.; Martín-Matute, B. ACS Catal. 2015, 5, 708
[66] Cadierno, V.; Francos, J.; Gimeno, J.; Nebra, N. Chem. Commun. 2007, 2, 536.
[67] Sahli, Z.; Sundararaju, B.; Achard, M.; Bruneau, C. Org. Lett. 2011, 13, 3964.
[68] Bizet, V.; Pannecoucke, X.; Renaud, J. L.; Cahard, D. Adv. Synth. Catal. 2013, 355, 1394.
[69] Shoola, C. O.; Del Mactro, T.; Wu, R.-Q.; Sowa. Jr, J. R. Eur. J. Org. Chem. 2015, 8, 1670.
[70] Colbon, P.; Ruan, J.-R.; Purdie, M.; Mulholl, K.; Xiao, J.-L. Org. Lett. 2011, 13, 5456.
[71] Li, H.-Q.; Achard, M.; Bruneau, C.; Sortais, J.-B.; Darcel, C. RSC Adv. 2014, 4, 25892.
[72] Ren, K.; Hu, B.; Zhao, M.-M.; Tu, Y.-H.; Xie, X.-M.; Zhang, Z.-G. J. Org. Chem. 2014, 79, 2170.
[73] Nakamura, Y. S.; Ohta, T. S.; Oe, Y. H. Chem. Commun. 2015, 51, 7459.

过渡金属催化烯丙醇异构化反应的研究进展

Transition Metal Catalyzed Isomerization Reaction of Allylic Alcohols

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