金属催化不饱和烃的官能化应用于吡咯烷和吡咯啉类化合物的合成
收稿日期: 2018-02-01
修回日期: 2018-02-24
网络出版日期: 2018-03-08
基金资助
国家自然科学基金（No.21572129）资助项目.
Metal-Catalyzed Unsaturated Hydrocarbon Functionalization Applied in the Synthesis of Pyrrolidines and Pyrrolines
Received date: 2018-02-01
Revised date: 2018-02-24
Online published: 2018-03-08
Supported by
Project supported by the National Natural Science Foundation of China (No. 21572129).
张金刚 , 吴正兴 , 谢芳 , 张万斌 . 金属催化不饱和烃的官能化应用于吡咯烷和吡咯啉类化合物的合成[J]. 有机化学, 2018 , 38(6) : 1319 -1326 . DOI: 10.6023/cjoc201802001
Pyrrolidines and pyrrolines, as important building blocks, are widely applied in the fields of medicine, agriculture and materials. Many synthetic methods for the preparation of pyrrolidines and pyrrolines have been reported over the past few years. Recently, following the rapid development of organometallic chemistry, the metal-catalyzed functionalization of unsaturated hydrocarbons has gradually become the research focus of organic synthesis methodology, due to the high efficiency and diversity of functionalization. Therefore the constructions of pyrrolidines and pyrrolines using metal-catalyzed unsaturated hydrocarbon functionalization are important and very useful. The development of metal-catalyzed functionalizations of different types of unsaturated hydrocarbons for the synthesis of pyrrolidines and pyrrolines is summarized.
Key words： metal-catalyzed; unsaturated hydrocarbon; functionalization; pyrrolidine; pyrroline
[1] (a) Kini, G. D.; Hennen, W. J.; Robins, R. K. J. Org. Chem. 1986, 51, 4436.
(b) Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633.
(c) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699.
(d) Ortega, H. G.; Crusats, J.; Feliz, M.; Ribo, J. M. J.Org.Chem. 2002, 67, 4170.
(e) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
(f) Shenoy, S. L.; Cohen, D.; Erkey, C.; Weiss, R. A. Ind. Eng. Chem. Res. 2002, 41, 1484.
(g) Lee, D.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 6870.
(h) Azioune, A.; Ben Slimane, A.; Ait Hamou, L.; Pleuvy, A.; Chehimi, M. M.; Perruchot, C.; Armes, S. P. Langmuir 2004, 20, 3350.
(i) Butler, M. S. J. Nat. Prod. 2004, 67, 2141.
(j) Magedov, I. V.; Luchetti, G.; Evdokimov, N. M.; Manpadi, M.; Steelant, W. F. A.; Van Slambrouck, S.; Tongwa, P.; Antipin, M. Y.; Kornienko, A. Bioorg. Med. Chem. Lett. 2008, 18, 1392.
(k) Gupta, R.; Walunj, S. S.; Tokala, R. K.; Parsa, K. V.; Singh, S. K.; Pal, M. Curr. Drug Targets 2009, 10, 71.
(l) More, S. S.; Krishna Mohan, T.; Sateesh Kumar, Y.; Syam Kumar, U. K.; Patel, N. B. Beilstein J. Org. Chem. 2011, 7, 831.
(m) Servillo, L.; Giovane, A.; Balestrieri, M. L.; Cautela, D.; Castaldo, A. D. J. Agric. Food Chem. 2011, 59, 274.
(n) Grychowska, K.; Satala, G.; Kos, T.; Partyka, A.; Colacino, E.; Chaumont-Dubel, S.; Bantreil, X.; Wesolowska, A.; Pawlowski, M.; Martinez, J.; Marin, P.; Subra, G.; Bojarski, A. J.; Lamaty, F.; Popik, P.; Zajdel, P. ACS Chem. Neurosci. 2016, 7, 972.
[2] (a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
(b) Cai, T.; Hu, B.; Lv, C. Chin.J. Org.Chem. 2005, 25, 1311(in Chinese). (蔡超君, 胡炳成, 吕春绪, 有机化学, 2005, 25, 1311.)
(c) Fan, H.; Peng, J. N.; Hamann, M. T.; Hu, J. F. Chem. Rev. 2008, 108, 264.
(d) Bhardwaj, V.; Gumber, D.; Abbot, V.; Dhiman, S.; Sharma, P. RSC Adv. 2015, 5, 15233.
(e) Khajuria, R.; Dham, S.; Kapoor, K. K. RSC Adv. 2016, 6, 37039.
(f) Feng, J. J.; Zhang, J. L. ACS Catal. 2016, 6, 6651.
(g) Wang, Q.; Chang, H.; Wei, W.; Liu, Q.; Gao, W.; Li, Y.; Li, X. Chin. J. Org. Chem. 2016, 36, 939(in Chinese). (王清宇, 常宏宏, 魏文珑, 刘强, 高文超, 李彦威, 李兴, 有机化学, 2016, 36, 939.)
(h) Gholap, S. S. Eur. J. Med. Chem. 2016, 110, 13. (i) Shimizu, S. Chem. Rev. 2017, 117, 2730.
(j) Wei, X.; Handoko, D. D.; Pather, L.; Methven, L.; Elmore, J. S. Food Chem. 2017, 232, 531.
(k) Gao, Y.; Xiao, Z.; Liu, L.; Huang, P. Chin. J. Org. Chem. 2017, 37, 1189(in Chinese). (高燕娇, 肖振华, 刘良先, 黄培强, 有机化学, 2017, 37, 1189.)
(l) Zhu, C.; Feng, J.; Zhang, J. Chin. J. Org. Chem. 2017, 37, 1165(in Chinese). (朱超泽, 冯见君, 张俊良, 有机化学, 2017, 37, 1165.)
[3] (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
(b) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161.
(c) Gribble, G. W. Acc. Chem. Res. 1998, 31, 141.
(d) Bataille, C. J. R.; Donohoe, T. J. Chem. Soc. Rev. 2011, 40, 114.
(e) Wang, J.; Cui, D. Chin. J. Org. Chem. 2016, 36, 1163(in Chinese). (王剑, 崔冬梅, 有机化学, 2016, 36, 1163.)
(f) Cai, S.-H.; Da, B.-C.; Zhou, J.-H.; Xu, Y.-H.; Loh, T.-P. Chin. J. Chem. 2016, 34, 1076.
(g) Wu, Z.; Zhang, W. Chin.J.Org. Chem. 2017, 37, 2250(in Chinese). (吴正兴, 张万斌, 有机化学, 2017, 37, 2250.)
[4] (a) Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484.
(b) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795.
(c) Huang, L. B.; Arndt, M.; Gooben K.; Heydt, H.; Gooben, L. J. Chem. Rev. 2015, 115, 2596.
[5] For allene:(a) Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 5421.
(b) Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496. For alkyne:
(c) Lutete, L. M.; Kadota, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 1622. For isolated alkene:
(d) Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070.
(e) Jiang, H. J.; Liu, K.; Yu, J.; Zhang, L.; Gong, L. Z. Angew. Chem., Int. Ed. 2017, 56, 11931.
(f) Gurak, John A.; Engle, Keary M. Synlett 2017, 28, 2057.
[6] (a) Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164.
(b) McDonald, R. I.; White, P. B.; Weinstein, A. B.; Tam, C. P.; Stahl, S. S. Org. Lett. 2011, 13, 2830.
[7] (a) Muniz, K.; Streuff, J.; Hövelmann, C. H.; Núnez, A. Angew. Chem., Int. Ed. 2007, 46, 7125.
(b) Sibbald, P. A.; Michael, F. E. Org. Lett. 2009, 11, 1147.
(c) Sibbald, P. A.; Rosewall, C. F.; Swartz, R. D.; Michael, F. E. J. Am. Chem. Soc. 2009, 131, 15945.
(d) Wang, Y. F.; Zhu, X.; Chiba S. J. Am. Chem. Soc. 2012, 134, 3679.
[8] (a) Donohoe, T. J.; Churchill, G. H.; Wheelhouse, K. M. P.; Glossop, P. A. Angew. Chem., Int. Ed. 2006, 45, 8025.
(b) Fuller, P. H.; Kim, J. W.; Chemler, S. R. J. Am. Chem. Soc. 2008, 130, 17638.
[9] (a) Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605.
(b) Sherman, E. S.; Chemler, S. R.; Tan, T. B.; Gerlits, O. Org. Lett. 2004, 6, 1573.
(c) Sherman, E. S.; Fuller, P. H.; Kasi, D.; Chemler, S. R. J. Org. Chem. 2007, 72, 3896.
(d) Zeng, W.; Chemler, S. R. J. Am. Chem. Soc. 2007, 129, 12948.
(e) Zeng, W.; Chemler, S. R. J. Org. Chem. 2008, 73, 6045.
(f) Rosewall, C. F.; Sibbald, P. A.; Liskin, D. V.; Michael, F. E. J. Am. Chem. Soc. 2009, 131, 9488.
(g) Sibbald, P. A.; Rosewall, C. F.; Swartz, R. D.; Michael, F. E. J. Am. Chem. Soc. 2009, 131, 15945.
(h) Lemen, G. S.; Wolfe, J. P. Org. Lett. 2010, 12, 2322.
(i) Zhang, G. Z.; Cui, L.; Wang, Y. Z.; Zhang, L. M. J. Am. Chem. Soc. 2010, 132, 1474.
(j) Brenzovich, W. E.; Benitez, D.; Lackner, A. D.; Shunatona, H. P.; Tkatchouk, E.; Goddard, W. A.; Toste, F. D. Angew. Chem., Int. Ed. 2010, 49, 5519.
(k) Tkatchouk, E.; Mankad, N. P.; Benitez, D.; Goddard, W. A.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 14293.
[10] (a) Ney, J. E.; Wolfe J. P. Angew. Chem., Int. Ed. 2004, 43, 3605.
(b) Ney, J. E.; Hay, M. B.; Yang, Q. F.; Wolfe, J. P. Adv. Synth. Catal. 2005, 347, 1614.
(c) Lemen, G. S.; Wolfe, J. P. Org. Lett. 2010, 12, 2322.
[11] (a) Schierle, K.; Vahle, R.; Steckhan, E. Eur. J. Org. Chem. 1998, 509.
(b) Field, L. D.; Messerle, B. A.; Wren, S. L. Organometallics 2003, 22, 4393.
(c) Burling, S.; Field, L. D.; Li, H. L.; Messerle, B. A.; Turner, P. Eur. J. Inorg. Chem. 2003, 3179.
(d) Burling, S.; Field, L. D.; Messerle, B. A.; Turner, P. Organometallics 2004, 23, 1714.
(e) Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Organometallics 2005, 24, 4241.
(f) Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P.; Failes, T. Organometallics 2007, 26, 2058.
(g) Burling, S.; Field, L. D.; Messerle, B. A.; Rumble, S. L. Organometallics 2007, 26, 4335.
(h) Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Dalton Trans. 2009, 3599.
(i) Beeren, S. R.; Dabb, S. L.; Messerle, B. A. J. Organomet. Chem. 2009, 694, 309. (j) Beeren, S. R.; Dabb, S. L.; Edwards, G.; Smith, M. K.; Willis, A. C.; Messerle, B. A. New J. Chem. 2010, 34, 1200.
(k) Rao, W. D.; Kothandaraman, P.; Koh, C. B.; Chan, P. W. H. Adv. Synth. Catal. 2010, 352, 2521.
(l) Rumble, S. L.; Page, M. J.; Field, L. D.; Messerle, B. A. Eur. J. Inorg. Chem. 2012, 2226.
(m) Rossom, W. V.; Matsushita, Y.; Ariga, K.; Hill, J. P. RSC Adv. 2014, 4, 4897.
(n) Shin, Y. H.; Maheswara, M.; Hwang, J. Y.; Kang, E. J. Eur. J. Org. Chem. 2014, 2305.
(o) Gao, P. C.; Sipos, G.; Foster, D.; Dorta, R. ACS Catal. 2017, 7, 6060.
(p) Timmerman, J. C.; Laulhe, S.; Widenhoefer, R. A. Org. Lett. 2017, 19, 1466.
[12] (a) Faulkner, A.; Bower, J. F. Angew. Chem., Int. Ed. 2012, 51, 1675. (b) Faulkner, A.; Scott, J. S.; Bower, J. F. J. Am. Chem. Soc. 2015, 137, 7224.
(c) Chen, C.; Hou, L. L.; Cheng, M.; Su, J. H.; Tong, X. F. Angew. Chem., Int. Ed. 2015, 54, 3092.
[13] (a) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444.
(b) Pugin, B.; Venanzi, L. M. J. Am. Chem. Soc. 1983, 105, 6877. (c) Shi, Z. Z.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 4892.
[14] (a) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 28, 45.
(b) Tsutsui, H.; Kitamura, M.; Narasaka, K. Bull. Chem. Soc. Jpn. 2002, 75, 1451.
/
| 〈 |
|
〉 |
