三氟甲烷磺酸钪催化醇对邻亚甲基苯醌的氧杂迈克尔加成反应
收稿日期: 2018-07-09
修回日期: 2018-08-26
网络出版日期: 2018-09-10
基金资助
山东省自然科学基金（No.ZR2017BB033）、山东省科学院青年科学基金（No.2018QN0030）和国家自然科学基金（No.51503118）资助项目.
Sc(OTf)3 Catalyzed Oxo-Michael Addition to o-Quinone Methides by Alcohols
Received date: 2018-07-09
Revised date: 2018-08-26
Online published: 2018-09-10
Supported by
Project supported by the Shandong Provincial Natural Science Foundation (No. ZR2017BB033), the Youth Science Funds of Shandong Academy of Sciences (No. 2018QN0030) and the National Natural Science Foundation of China (No. 51503118).
张硕 , 彭丹 , 赵宁 , 于一涛 , 王峰 , 刘海龙 , 伊港 . 三氟甲烷磺酸钪催化醇对邻亚甲基苯醌的氧杂迈克尔加成反应[J]. 有机化学, 2019 , 39(2) : 555 -560 . DOI: 10.6023/cjoc201807017
o-Quinone derivatives are not only a variety of active and important intermediate, but also widely used in the synthesis of natural products and medicinal chemistry. In the present study, the Sc(OTf)3 catalyzed oxo-Michael addition to o-quinone methides by alcohols was developed. The products were obtained in moderate to good yields (76%~97%) under mild conditions. Furthermore, the reaction could be scaled up to multigram scale.
Key words： o-quinone; scandium(III) triflate; oxo-Michael addition; green chemistry
[1] Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76, 9210.
[2] Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160.
[3] Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
[4] Wang, Z.; Sun, J. Synthesis 2015, 47, 3629.
[5] Guo, C.; Song, J.; Luo, S.; Gong, L. Z. Angew. Chem., Int. Ed., 2010, 49, 5558.
[6] Van De Water, R, W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
[7] Kulikov, A.; Arumugam, S.; Popik, V. V. J. Org. Chem. 2008, 73, 7611.
[8] Mattson, A. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 4508.
[9] Luan, Y.; Schaus, S. E. J. Am. Chem. Soc. 2012, 134, 19965.
[10] Shaikh, A. K.; Cobb, A. J. A.; Varounis, G. Org. Lett. 2012, 14, 584.
[11] Chen, M. W.; Gao, L. L.; Ye, Z. S.; Jiang, G. F.; Zhou, Y. G. Chem. Commun. 2013, 49, 1660.
[12] Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. A. Org. Lett. 2004, 6, 4049.
[13] Bai, W. J.; David, J. G.; Feng, Z. G.; Weaver, M. G.; Wu, K. L.; Pettus, T. R. R. Acc. Chem. Res. 2014, 47, 3655.
[14] Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
[15] Wang, Z.; Sun, J. Synthesis 2015, 47, 3629.
[16] Zhao, W.; Wang, Z.; Chu, B.; Sun, J. Angew. Chem., Int. Ed. 2015, 54, 1910.
[17] Huang, Y.; Hayashi, T. J. Am. Chem. Soc. 2015, 137, 7556.
[18] Wang, Z.; Ai, F.; Wang, Z.; Zhao, W.; Zhu, G.; Lin, Z.; Sun, J. J. Am. Chem. Soc. 2015, 137, 383.
[19] Wu, B.; Yu, Z.; Gao, X.; Lan, Y.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2017, 56, 4006.
[20] Chen, P.; Wang, K. l; Guo, W.; Liu, X.; Liu, Y.; Li, C. Angew. Chem., Int. Ed. 2017, 56, 3689.
[21] Nising, C. F.; Brase, S. Chem. Soc. Rev. 2008, 37, 1218.
[22] Nising, C. F.; Brase, S. Chem. Soc. Rev. 2012, 41, 988.
[23] Heravi, M. M.; Hajiabbasi, P. Mol. Diversity 2014, 18, 411.
[24] Gu, Q.; Rong, Z.-Q.; Zheng, C.; You, S. L. J. Am. Chem. Soc. 2010, 132, 4056.
[25] Rubush, D. M.; Morges, M. A.; Rose, B. J.; Thamm, D. H.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 13554.
[26] Shi, Y. L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499.
[27] Liang, M.; Zhang, S.; Jia, J.; Tung, C.-H.; Wang, J. W.; Xu, Z. H. Org. Lett. 2017, 19, 2526.
[28] Lai, Z. W.; Wang, Z. B.; Sun, J. W. Org. Lett. 2015, 17, 6058.
/
| 〈 |
|
〉 |
