Chinese Journal of Organic Chemistry >
Catalytic Asymmetric Synthesis of Chiral Acetals
Received date: 2015-03-09
Revised date: 2015-03-30
Online published: 2015-04-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202092) and the Startup Foundation from China Three Gorges University (No. KJ2012B080).
Acetals are common building blocks of many drugs and natural product molecules. It was found that the biological activity of chiral acetals is usually superior to their racemates. The catalytic asymmetric synthesis of chiral acetals is challenge for its racemization and attracts attention until recent years. In this review, the recent studies on catalytic asymmetric synthesis of chiral aminals, N,O-acetals, N,S-acetals, O,O-acetals, as well as its application in synthesis of chiral drugs containing acetal moieties are reviewed.
Du Peng , Zhou Haifeng , Shen Guanshuo , Zou Kun . Catalytic Asymmetric Synthesis of Chiral Acetals[J]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1641 -1649 . DOI: 10.6023/cjoc201503010
[1] Verdel, B. M.; Souverein, P. C.; Egberts, A. C. G.; Leufkens, H. G. M. Ann. Pharm. 2006, 40, 1040.
[2] Mavragani, C. P.; Moutsopoulos, H. M. Clin. Rev. Allergy Immunol. 2007, 32, 287.
[3] Felix, W.; Rimbach, G.; Wengenroth, H. Arzneim. Forsch. 1969, 19, 1860.
[4] Chinigo, G. M.; Paige, M.; Grindrod, S.; Hamel, E.; Dakshanamurthy, S.; Chruszcz, M.; Minor, W.; Brown, M. L. J. Med. Chem. 2008, 51, 4620.
[5] (a) Liu, N.; Yang, L.; Yang, B.; Wang, J.; Chen. X.; Wu, Q. Chin. J. Org. Chem. 2014, 34, 2523 (in Chinese). (刘宁宁, 杨玲, 杨蓓, 王金棒, 陈雪, 武钦佩, 有机化学, 2014, 34, 2523.) (b) Wang, C.; Li, Y.; Jia, G.; Lu, S.; Liu, Y.; Li, C. Acta Chim. Sinica 2013, 71, 36 (in Chinese). (王长号, 李英豪, 贾国卿, 卢胜梅, 刘李灿, 化学学报, 2013, 71, 36.) (c) Chen, J.; Liu, Q.; Dai, X.; Nie, L.; Fang, H.; Wu, X. Chin. J. Org. Chem. 2013, 33, 1 (in Chinese). (陈杰, 刘钦, 戴小鸯, 聂凛凛, 房辉辉, 吴小余, 有机化学, 2013, 33, 1.) (d) Feng, T.; Si, C.; Liu, R.; Fan, X.; Wei, B. Chin. J. Org. Chem. 2013, 33, 1291 (in Chinese). (冯涛, 司长梅, 刘如成, 范翔, 魏邦国, 有机化学, 2013, 33, 1291.) (e) Liu, N.; Chen, X.; Zhang, Q.; Wu, Q. Chin. J. Org. Chem. 2014, 34, 1364 (in Chinese). (刘宁宁, 陈曦, 张青山, 武钦佩, 有机化学, 2014, 34, 1364.)
[6] (a) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696. (b) Liang, Y.; Rowland, E. B.; Rowland, G. B.; Perman, J. A.; Anitlla, J. C. Chem. Commun. 2007, 43, 4477.
[7] Hatano, M.; Ozaki,T.; Sugiura, Y.; Ishihara, K. Chem. Commun. 2012, 48, 4986.
[8] Cheng, X.; Vellalath, S.; Goddard, R.; List, B. J. Am. Chem. Soc. 2008, 130, 15786.
[9] Rueping, M.; Antonchick, A. P.; Sugiono, E.; Grenader, K. Angew. Chem., Int. Ed. 2009, 48, 908.
[10] Huang, D.; Li, X.; Xu, F.; Li, L.; Lin, X. ACS Catal. 2013, 3, 2244.
[11] Cheng, D. J.; Tian, Y.; Tian, S. K. Adv. Synth. Catal. 2012, 354, 995.
[12] (a) Prakash, M.; Kesavan, V. Org. Lett. 2012, 14, 1896. (b) Prakash, M.; Jayakumar, S.; Kesavan, V. Synthesis 2013, 2265.
[13] Jiang, Y.; Liu, Y.; Tu, S. J.; Shi, F. Tetrahedron: Asymmetry 2013, 24, 1286.
[14] Neel, A. J.; Hehn, J. P.; Tripet, P. F.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 14044.
[15] He, Y. P.; Du, Y. L.; Luo, S. W.; Gong, L. Z. Tetrahedron Lett. 2011, 52, 7064.
[16] He, Y.; Cheng, C.; Chen, B.; Duan, K.; Zhuang, Y.; Yuan, B.; Zhang, M.; Zhou, Y.; Zhou, Z.; Su, Y. J.; Cao, R.; Qiu, L. Org. Lett. 2014, 16, 6366.
[17] Patil, N. T.; Mutyala, A. K.; Konala, A.; Tella, R. B. Chem. Commun. 2012, 48, 3094.
[18] (a) He, Y. P.; Wu, H.; Chen, D. F.; Yu, J.; Gong, L. Z. Chem. Eur. J. 2013, 19, 5232. (b) Chen, D. F.; Han, Z. Y.; Zhou, X. L.; Gong, L. Z. Acc. Chem. Res. 2014, 47, 2365.
[19] Li, G.; Fronczek, F. R.; Antilla, J. C. J. Am. Chem. Soc. 2008, 130, 12216.
[20] Li, T. Z.; Wang, X. B.; Sha, F.; Wu, X. Y. Tetrahedron 2013, 69, 7314.
[21] Vellalath, S.; Coric, I.; List, B. Angew. Chem., Int. Ed. 2010, 49, 9749.
[22] Kim, H.; Rhee, Y. H. J. Am. Chem. Soc. 2012, 134, 4011.
[23] Zhou, F.; Zeng, X. P.; Wang, C.; Zhao, X. L.; Zhou, J. Chem. Commun. 2013, 49, 2022.
[24] Ingle, G. K.; Mormino, M. G.; Wojtas, L.; Antilla, J. C. Org. Lett. 2011, 13, 4822.
[25] Wang, H. Y.; Zhang, J. X.; Cao, D. D.; Zhao, G. ACS Catal. 2013, 3, 2218.
[26] Fang, X.; Li, Q. H.; Tao, H.Y.; Wang, C. J. Adv. Synth. Catal. 2013, 355, 327.
[27] Qian, H.; Sun, J. Asian J. Org. Chem. 2014, 3, 387.
[28] Nakamura, S.; Takahashi, S.; Nakane, D.; Masuda, H. Org. Lett. 2015, 17, 106.
[29] (a) Wang, X.; Han, Z.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 936. (b) Wang, X.; Guo, P.; Wang, X.; Wang, Z.; Ding, K. Adv. Synth. Catal. 2013, 355, 2900.
[30] (a) Coric, I.; List, B. Nature 2012, 483, 315. (b) Kim, J. H.; Coric, I.; Vellalath, S.; List, B. Angew. Chem., Int. Ed. 2013, 52, 4474.
[31] Sun, Z.; Winschel, G. A.; Borovika, A.; Nagorny, P. J. Am. Chem. Soc. 2012, 134, 8074.
[32] Wu, H.; He, Y. P.; Gong, L. Z. Org. Lett. 2013, 15, 460.
[33] Cala L.; Mendoza, A.; Fananas, F. J.; Rodríguez, F. Chem. Commun. 2013, 49, 2715.
[34] Uzunov, D. P.; Zivkovich, I; Pirkle, W. H.; Costa, E.; Guidotti, A. J. Pharm. Sci. 1995, 84, 937.
[35] Saitoh, F.; Nishida, H.; Mukaihira, T.; Aikawa, K.; Mikami, K. Eur. J. Org. Chem. 2006, 10, 2269.
/
| 〈 |
|
〉 |
