Progress on the Asymmetric Diels-Alder Reaction of α,β-Unsaturated Carbonyl Compounds

doi:10.6023/cjoc201601027

Abstract

Diels-Alder reaction is a [4+2] concerted cycloaddition reaction, which has attracted considerable attention since its discovery. Asymmetric Diels-Alder reaction is an effective method for synthesis of chiral intermediates, so it was widely applied in the total synthesis of drugs and natural products. α,β-Unsaturated carbonyl compounds are a kind of highly reactive versatile intermediates in organic synthesis, according to its structural characteristics and catalytic types, recent advances in asymmetric normal electron-demand Diels-Alder reaction of α,β-unsaturated carbonyl compounds are reviewed in this paper.

Key words: asymmetric Diels-Alder reaction, natural product, organic synthesis, α,β-unsaturated carbonyl compounds

Cite this article

Liu Wenxiang, Wu Yuqiang, Li Lingzhi, Li Xia. Progress on the Asymmetric Diels-Alder Reaction of α,β-Unsaturated Carbonyl Compounds[J]. Chin. J. Org. Chem., 2016, 36(7): 1501-1512.

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References

[1] Diels, O.; Alder, K. Ann. 1928, 460, 98.
[2] Wang, C.; Liu, W.-H.; Zhou, X.; Li, Y.-M.; Li, Y-.P. Prog. Chem. 2009, 9, 1857 (in Chinese). (王春, 刘伟华, 周欣, 李越敏, 李云鹏, 化学进展, 2009, 9, 1857.)
[3] (a) Yates, P. J. Am. Chem. Soc. 1960, 82, 4436.
(b) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
(c) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333.
[4] Jeffrey, D.W. Chem. Rev. 1996, 96, 167.
[5] Wang, S.-M.; Li, Y.; Guo, R.-X.; Li, L.-G.; Chang, H.-P.; Li, Z.; Shi, Q.-W. Nat. Prod. Res. Devel. 2013, 25, 698 (in Chinese). (王思明, 郭瑞霞, 李力更, 常和平, 李骘, 史清文, 李勇, 天然产物研究与开发, 2013, 25, 698.)
[6] Dennis, E. D. Clin. Pharmacol. Ther. 1986, 40, 125.
[7] (a) Lan, Z.-W.; Li, Y.; Chen, H.; Xiao, Y.-F. Organic Chemistry, Ocean Press, Beijing, 2004 (in Chinese). (蓝仲薇, 李瑛, 陈华, 肖友发, 有机化学, 海洋出版社, 北京, 2004.)
(b) Ou, Y.-Y.; Yu, H.-F.; Dong, D.-W.; Liu, Q. J. Northeast Normal. Univ. 2006, 38, 67 (in Chinese). (欧阳艳, 于海丰, 董德文, 刘群, 东北师大学报, 2006, 38(1), 67.)
(c) Fuchs, N.; Augustin, M.; Humam, M.; Alexakis, A.; Taras, R.; Gladiali, S. Tetrahedron 2005, 16, 3143.
[8] (a) Liu, W.-M.; Wang, Q.-F.; Zhang, S.-Y. Chin. J. Org. Chem. 2007, 27, 862 (in Chinese). (柳文敏, 王巧峰, 张生勇, 有机化学, 2007, 27, 862.)
(b) Mendelovici, M.; Glotter, E. J. Chem. Soc., Perkin Trans. 1 1992, 1735.
[9] (a) Pei, W. J. Yanbian Univ. 1997, 23, 29 (in Chinese). (裴文, 延边大学学报, 1997, 23, 29.)
(b) Pei, W.; Xun, M. -Z.; Sun, L.; Ni, Z.-M.; Piao, H.-R. Chin. J. Synth. Chem. 2002, 10, 49 (in Chinese). (裴文, 徐明哲, 孙莉, 倪哲明，朴虎日, 合成化学, 2002, 10, 49.)
(c) Pei, W.; Sun, L.; Wang H.-B.; Deng, Q.; Sun, L. Chin. J. Org. Chem. 2006, 26(5), 727 (in Chinese). (裴文, 孙莉, 王海滨, 邓琼，孙莉, 有机化学, 2006, 26(5), 727.)
[10] (a) Xu, K.-X. Refined Chemical Raw Materials and Intermediate Manual, Chemical Industry Press, Beijing, 1998 (in Chinese). (徐克勋, 精细有机化工原料及中间体手册, 化学工业出版社, 北京, 1998.)
(b) Sun, B.-G.; He, J. Perfume Chemistry Process, Chemical Industry Press, Beijing, 2004 (in Chinese). (孙保国, 何坚, 香料化学与工艺, 化学工业出版社, 北京, 2004.)
[11] Woodward, R.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395.
[12] Fukui, K.; Yonezawa, T.; Shingu, H. J. Chem. Phys. 1952, 20, 722.
[13] Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908.
[14] Evans, D.; Chapman, K.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261.
[15] Oppolzer, W.; Christian,C.; Gerald, B. Preliminary Commun. 1984, 67, 1397.
[16] Enholm, E. J.; Jiang, S. J. Org. Chem. 2000, 65, 4756.
[17] Bañuelos, P.; García, J. M.; Enrique, G. B.; Palomo, C.; Herrero, A.; Odriozola, J. M.; Oiarbidet, M.; Razkin, J. J. Org. Chem. 2010, 75, 1458.
[18] David, S.; Eustache, J.; Lubineau, A. J. Chem. Soc., Perkin Trans. 1 1974, 2274.
[19] Bednarski, M.; Danishefsky, S.; J. Am. Chem. Soc. 1983, 105, 6968.
[20] (a) Gupta, R. C.; Harland, P. A.; Stoodley, R. J. J. Chem. Soc. Chem. Commun. 1983, 754.
(b) Gupta, R. C.; Harland, P. A.; Stoodley, R. J. Tetrahedron 1984, 40, 4657.
(c) Gupta, R. C.; Slawin, A. M. Z.; Stoodley, R. J.; Williams, D. J. J. Chem. Soc. Chem. Commun. 1986, 668.
(d) Gupta, R. C.; Slawin, A. M. Z.; Stoodley, R. J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1986, 1116.
(e) Gupta, R. C.; Raynor, C. M.; Stoodley, R. J.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1988,1773.
(f) Gupta, R. C.; Larsen, D. S.; Stoodley, R. J.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1989, 739.
[21] Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1999, 121, 9562.
[22] (a) Davis, F. A.; JenkinsJr, R. H.; Awad, S. B.; Stringer, O. D.; Watson, W. H.; Galloy, J. J. Am. Chem. Soc. 1982, 104, 5412.
(b) Kagan, H, B.; Riant, O. Chem. Rev. 1992, 92, 1007.
(c) Dias, L, C. J. Brazilian Chem. Soc. 1997, 8, 289.
(d) Ahrendt, K. K.; Borths, C. J.; Macmillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
(e) Li, G.-L.; Liang, T.; Wojtas, L.; Antilla, J. C. Angew. Chem., Int. Ed. 2013, 52, 4628.
(f) Hatano, M.; Hayashi, K.; Sakamoto, T.; Makino, Y.; Ishihara, K. Synlett 2016, 27, A-G.
[23] Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K. J. Am. Chem. Soc. 1969, 91, 5675.
[24] Corey, E. J.; Imwinkelried, R.; Pikul, S. J. Am. Chem. Soc. 1989, 111, 5493.
[25] Corey, E. J.; Loh, T. P. J. Am. Chem. Soc. 1991, 113, 8966.
[26] Corey, E.J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807.
[27] Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502.
[28] Hu, Q. Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984.
[29] Chapuis, C.; Jurczak, J. Helv. Chim. Acta 1987, 70, 436.
[30] Ishihara, J.; Nakadachi, S.; Watanabe, Y.; Hatakeyama, S. J. Org. Chem. 2015, 80, 2037.
[31] Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
[32] Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735.
[33] Orimoto, K.; Oyama, H.; Namera, Y.; Niwa, T.; Nakada, M. Org. Lett. 2013, 15, 768
[34] Harada, S.; Morikawa, T.; Nishida, A. Org Lett. 2013, 15, 5314.
[35] Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668.
[36] (a) Noyori, R. Adv. Synth. Catal. 2001, 343, 1.
(b) Noyori, R. Chem. Commun. 2005, 1807.
[37] (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
(b) Zhang, W.; Chi, Y.; Zhang, X. Acc. Chem. Res. 2007, 40, 1278.
(c) Chan, A. S. C.; Hu, W.; Pai, C. C.; Lau, C. P.; Jiang, Y.; Mi. A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570.
(d) Wu, J.; Chan, A. S. C. Acc. Chem. Res. 2006, 39, 711.
(e) Xie, J. H.; Zhou, Q. L. Acc. Chem. Res. 2008, 41, 581.
(f) Ding, K.; Han, Z.; Wang, Z. Chem.-Asian J. 2009, 4, 32.
(g) Han, Z.; Wang, Z.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2009, 48, 5345.
(h) Wang, D.; Hu, X.; Huang, J.; Deng, J.; Yu, S.; Duan, Z.; Xu, X.; Zheng, Z. Angew. Chem., Int. Ed. 2007, 46, 7810.
(i) Zhou, J.; Tang, Y. J. Am. Chem. Soc. 2002, 124, 9030.
[38] Merino, P.; Marqués-López, E.; Tejero, T.; Herrera, R, P. Synthesis 2010, 1.
[39] Hine, J.; Linden, S. M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096.
[40] Kelly, T. R.; Meghani, P.; Ekkundi, V. S. Tetrahedron Lett. 1990, 31, 3381.
[41] Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
[42] Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5846.
[43] Li, C.; Yu, X., Lei, X. Org. Lett. 2010, 12, 4284.
[44] (a) Liu, H.; Cun, L. F.; Mi, A. Q.; Jiang, Y. Z.; Gong, L. Z. Org. Lett. 2006, 8, 6023.
(b) Akiyama, T.; Tamura, Y.; Itoh, J. Synlett 2006, 141.
[45] Han, Z.-Y.; Chen, D.-F.; Wang, Y.-Y.; Guo, R.; Wang, P.-S.; Wang, C.; Gong, L.-Z. J. Am. Chem. Soc. 2012, 134, 6532.
[46] Wang, Y.; Tu, M.-S., Lei, Y., Sun, M.; Shi, F. J. Org. Chem. 2015, 80, 3223.
[47] (a) Momiyama, N.; Konno, T.; Furiya, Y.; Iwamoto, T.; Terada, M. J. Am. Chem. Soc. 2011, 133, 19294.
(b) Wu, H.; He, Y.-P.; Shi, F. Synthesis 2015, 47, 1990.
[48] Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626.
[49] Schuster, T.; Bauch, M.; Dürner, G.; Gobel, M. W. Org Lett. 2000, 2, 179.
[50] Marko, W.; Gerd, D.; Bats, J. W.; Gobel, M. W. J. Org. Chem. 2010, 75, 2718.
[51] (a) Zheng, C.-W.; Lu, Y.-P.; Zhang, J.-K.; Chen, X.-K.; Chai, Z.; Ma, W.-Y.; Zhao, G. Chemistry 2010, 16, 5853.
(b) Singh, R. P.; Bartelson, K.; Wang, Y.; Su, H.; Lu, X.; Deng, L. J. Am. Chem. Soc. 2008, 130, 2422.
(c) Chen, H. -T.; Trewyn, B. G.; Wiench, J. W.; Pruski, M.; Lin, V. S. Y. Top. Catal. 2010, 53, 187.
(d) Siau, W. Y.; Wang, J. Catal. Sci. Technol. 2011, 1, 1298.
(e) Jiang, X.-X.; Shi, X.-M.; Wang, S.-L.; Sun, T.; Cao, Y.-M.; Wang, R. Angew. Chem., Int. Ed. 2012, 51, 2084.
(f) Mao, Z.-J.; Lin, A.-J.; Shi, Y.; Mao, H.-B.; Li, W.-P.; Cheng, Y.-X.; Zhu, C.-J. J. Org. Chem. 2013, 78, 10233.
(g) Held, F. E.; Tsogoeva, S. B. Catal. Sci. Technol. 2016, 6, 645.
[52] Tan, B.; Hernandez-Torres, G.; Barbas, C. F. J. Am. Chem. Soc. 2011, 133, 12354.
[53] Baum, J. S.; Viehe, H. G. J. Org. Chem. 1976, 41, 183.
[54] Ahrendt, K. A.; Borths, C. J.; Macmillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
[55] Northrup, A. B.; Macmillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
[56] Abbasov, M. E.; Hudson, B. M.; Tantillo, D. J.; Romo, D. J. Am. Chem. Soc. 2014, 136, 4492
[57] Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510.
[58] Maruoka, K.; Sakurai, M.; Fujiwara, J.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 4895.
[59] Wipf, P.; Jung, J. K. J. Org. Chem. 2000, 65, 6319.
[60] (a) Nomura, T.; Hano, Y. Nat. Prod. Rep. 1994, 11, 205.
(b) Nomura, T. Pure Appl. Chem. 1999, 71, 1115.
(c) Nomura, T.; Hano, Y.; Ueda, S. Stud. Nat. Prod. Chem. 1995, 17, 451.
(d) Nomura, T. Pure Appl. Chem. 1999, 71, 1115.
[61] Corbett, J. L.; Weavers, R. T. Synth. Commun. 2008, 38, 489.
[62] (a) Jung, E. M.; Lee, Y. R. Bull. Korean Chem. Soc. 2008, 29, 1199.
(b) Chee, C. F.; Abdullah, I.; Buckle, M. J. Tetrahedron Lett. 2010, 51, 495.
(c) Chee, C. F.; Lee, Y. K.; Buckle, M. J. C; Rahman, N. A. Tetrahedron Lett. 2011, 52, 1797.
(d) Gunawan, C.; Rizzacasa, M. A. Org. Lett. 2010, 12, 1388.
[63] Cong, H.; Ledbetter, D.; Rowe, G. T.; Caradonna, J. P.; Porco, Jr. J. A. J. Am. Chem. Soc. 2008, 130, 9214.
[64] Cong, H.; Becker, C. F.; Elliott, S. J.; Grinstaff, M. W.; Porco,Jr. J. A. J. Am. Chem. Soc. 2010, 132, 7514.
[65] Boonsri, S.; Gunawan, C.; Krenske, E. H. Rizzacasa. M. A. Org. Biomol. Chem. 2012, 10, 6010.
[66] Han, J.; Jones, A. X.; Lei, X. Synthesis 2014, 47.
[67] Li, X.; Han, J.; Jones, A. X.; Lei, X. J. Org. Chem. 2016, 8, 458.
[68] (a) Han, J.; Li, X.; Guan, Y.; Zhao, W.; Wulff, W.; Lei, X. Angew. Chem. Int. Ed. 2014, 53, 9257.
(b) Lei, G.; Han, J.; Lei, X. Org. Lett., 2016, 18, 360.
[69] (a) Pingfan, Li.; Yamamoto. H. J. Am. Chem. Soc. 2009, 131, 16628.
(b) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3185.
(c) Jiang, X.-X.; Wang, R. Chem. Rev. 2013, 113, 5515.
[70] Wei, W.-D. Organic Chemical Raw Materials, Chemical Industry Press, Beijing, 1999 (in Chinese). (魏文德, 有机化工原料大全(中卷), 化学工业出版社, 北京, 1999.)

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