OALib Journal期刊
ISSN: 2333-9721
费用：99美元

投递稿件

查看量	下载量

相关文章
更多...

有机化学 2014

烯丙基磷叶立德与羰基化合物的Vinylogous类型有机反应研究进展有机化学

DOI: 10.6023/cjoc201407027, PP. 2438-2447

徐四龙, 贺峥杰

Keywords: 磷叶立德,插烯规则,Wittig反应,环化反应

Full-Text Cite this paper Add to My Lib

Abstract:

烯丙基磷叶立德(allylicphosphorusylides)是一类具有丰富反应性的有机中间体.由于碳负离子离域,烯丙基磷叶立德可通过γ位碳负离子参与亲核进攻,从而实现vinylogous(插烯)类型有机合成反应.综述了烯丙基磷叶立德与羰基化合物的vinylogous类型反应,具体包括vinylogousWittig烯化反应以及多种环化反应.这些反应拓展了烯丙基磷叶立德在有机合成中的应用,并提供构筑多种重要有机功能分子的新方法.

References

[1]	Fuson, R. C. Chem. Rev. 1935, 16, 1.
[2]	Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076.
[3]	Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
[4]	Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
[5]	Schneider, D. F.; Venter, A. C. Synth. Commun. 1999, 29, 1303.
[6]	Corey, E. J.; Erickson, B. W. J. Org. Chem. 1974, 39, 821.
[7]	Date, S. M.; Ghosh, S. K. Angew. Chem., Int. Ed. 2007, 46, 386.
[8]	(a) Xu, S.; He, Z. Chin. J. Org. Chem. 2012, 32, 1159 (in Chinese). (徐四龙, 贺峥杰, 有机化学, 2012, 32, 1159.) (b) Xu, S.; He, Z. RSC Adv. 2013, 3, 16885. (c) Xu, S.; He, Z. Sci. China, Chem. 2010, 40, 856 (in Chinese). (徐四龙, 贺峥杰, 中国科学: 化学, 2010, 40, 856.)
[9]	Khong, S. N.; Tran, Y. S.; Kwon, O. Tetrahedron 2010, 66, 4760.
[10]	Liang, Y.; Liu, S.; Yu, Z.-X. Synlett 2009, 905.
[11]	Xu, S.; Zhou, L.; Zeng, S.; Ma, R.; Wang, Z.; He, Z. Org. Lett. 2009, 11, 3498.
[12]	Qin, Z.; Ma, R.; Xu, S.; He, Z. Tetrahedron 2013, 69, 10424.
[13]	Ma, R.; Xu, S.; Tang, X.; Wu, G.; He, Z. Tetrahedron 2011, 67, 1053.
[14]	(a) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447. (b) Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659.
[15]	Zhou, R.; Wang, C.; Song, H.; He, Z. Org. Lett. 2010, 12, 976.
[16]	Chen, Z.; Zhang, J. Chem.-Asian J. 2010, 5, 1542.
[17]	Xie, P.; Li, E.; Zheng, J.; Li, X.; Huang, Y.; Chen, R. Adv. Synth. Catal. 2013, 355, 161.
[18]	(a) Bohlmann, F.; Zdero, C. Chem. Ber. 1973, 106, 3779. (b) Büchi, G.; Wüest, H. Helv. Chim. Acta 1971, 54, 1767. (c) Padwa, A.; Brodsky, L. J. Org. Chem. 1974, 39, 1318.
[19]	Martin, S. F.; Desai, S. R. J. Org. Chem. 1977, 42, 1664.
[20]	Wang, Q.; Sun, X.; Zheng, J.; Tang, Y. Chin. J. Chem. 2010, 28, 1618.
[21]	Ye, L.-W.; Wang, S.-B.; Wang, Q.-G.; Sun, X.-L.; Tang, Y.; Zhou, Y.-G. Chem. Commun. 2009, 3092.
[22]	Yadav, J. S.; Srinivas, D. Tetrahedron Lett. 1997, 38, 7789.
[23]	(a) Himeda, Y.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Chem. Commun. 1995, 449. (b) Himeda, Y.; Yamataka, H.; Ueda, I.; Hatanaka, M. J. Org. Chem. 1997, 62, 6529.
[24]	Hatanaka, M.; Himeda, Y.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1993, 2269.
[25]	Wang, P.; Liao, S.; Zhu, J.-B.; Tang, Y. Chem. Commun. 2014, 50, 808.
[26]	Zhang, Y. Univ. Chem. 2002, 17, 55 (in Chinese). (张殷全, 大学化学, 2002, 17, 55.)
[27]	Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221.
[28]	Kolodiazhnyi, O. I. Phosphorus Ylides: Chemistry and Application in Organic Synthesis, Wiley-VCH, New York, 1999.
[29]	Howe, R. K. J. Am. Chem. Soc. 1971, 93, 3457.
[30]	(a) Tamura, R.; Saegusa, K.; Kakihana, M.; Oda, D. J. Org. Chem. 1988, 53, 2723. (b) Tamura, R.; Kato, M.; Saegusa, K.; Kakihana, M.; Oda, D. J. Org. Chem. 1987, 52, 4121. (c) Robiette, R.; Richardson, J.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2006, 128, 2394.
[31]	Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87.
[32]	(a) He, Z.; Tang, X.; He, Z. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1518. (b) Xu, S.; Chen, R.; He, Z. J. Org. Chem. 2011, 76, 7528.
[33]	(a) Fan, Y. C.; Kwon, O. Chem. Commun. 2013, 49, 11588. (b) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927. (c) Tang, Q.; Tu, A.; Deng, Z.; Hu, M.; Zhong, W. Chin. J. Org. Chem. 2013, 33, 954 (in Chinese). (唐谦, 涂爱平, 邓真真, 胡梦莹, 钟为慧, 有机化学, 2013, 33, 954.) (d) Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724. (e) Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005. (f) Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102. (g) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140. (h) Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520. (i) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035. (j) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
[34]	Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Chem.-Eur. J. 2009, 15, 8698.
[35]	Xiao, H.; Chai, Z.; Yao, R.-S.; Zhao, G. J. Org. Chem. 2013, 78, 9781.
[36]	(a) Li, E.; Huang, Y. Chem.-Eur. J. 2014, 20, 3520. (b) Li, E.; Jia, P.; Liang, L.; Huang, Y. ACS Catal. 2014, 4, 600. (c) Li, E.; Huang, Y. Chem. Commun. 2014, 50, 948. (d) Li, E.; Huang, Y.; Liang, L.; Xie, P. Org. Lett. 2013, 15, 3138. (e) Gicquel, M.; Gomez, C.; Retailleau, P.; Voituriez, A.; Marinetti, A. Org. Lett. 2013, 15, 4002.
[37]	Du, Y.; Lu, X.; Zhang, C. Angew. Chem., Int. Ed. 2003, 42, 1035.
[38]	Wang, T.; Shen, L.-T.; Ye, S. Synthesis 2011, 3359.
[39]	(a) Tian, J.; Zhou, R.; Sun, H.; Song, H.; He, Z. J. Org. Chem. 2011, 76, 2374. (b) Zhou, R.; Duan, C.; Yang, C.; He, Z. Chem.-Asian J. 2014, 9, 1183. (c) Tian, J.; Sun, H.; Zhou, R.; He, Z. Chin. J. Chem. 2013, 31, 1348.
[40]	Xie, P.; Huang, Y.; Chen, R. Chem.-Eur. J. 2012, 18, 7362.
[41]	(a) Shi, M.; Hu, F.-L.; Wei, Y. Chem. Commun. 2014, 50, 8912. (b) Zhang, X. N.; Deng, H. P.; Huang, L.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 8664.
[42]	Dauben, W. G.; Hart, D. J.; Ipaktschi, J.; Kozikowski, A. P. Tetrahedron Lett. 1973, 14, 4425.
[43]	Dauben, W. G.; Ipaktschi, J. J. Am. Chem. Soc. 1973, 95, 5088.
[44]	(a) Ye, L.-W.; Han, X.; Sun, X.-L.; Tang, Y. Tetrahedron 2008, 64, 8149. (b) Shu, Z.-C.; Zhu, J.-B.; Liao, S.; Sun, X.-L.; Tang, Y. Tetrahedron 2013, 69, 284.
[45]	Liu, S.; Chen, W.; Luo, J.; Yu, Y. Chem. Commun. 2014, 50, 8539.
[46]	Bennani, Y. L.; Boehm, M. F. J. Org. Chem. 1995, 60, 1195.
[47]	Himeda, Y.; Ueda, I.; Hatanaka, M. Chem. Lett. 1996, 25, 71.
[48]	(a) Hatanaka, M.; Himeda, Y.; Ueda, I. J. Chem. Soc., Chem. Commun. 1990, 526. (b) Hatanaka, M.; Himeda, Y.; Imashiro, R.; Tanaka, Y.; Ueda, I. J. Org. Chem. 1994, 59, 111. (c) Hatanaka, M.; Himeda, Y.; Ueda, I. Tetrahedron Lett. 1991, 32, 4521.
[49]	Ouyang, K.; Xi, Z. Acta Chim. Sinica 2013, 71, 13 (in Chinese). (欧阳昆冰, 席振峰, 化学学报, 2013, 71, 13.)

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133