Synthesis of α-Trifluoromethyl-α-hydroxyl Weinreb Amides

doi:10.6023/cjoc201606034

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 103-109.DOI: 10.6023/cjoc201606034 Previous Articles Next Articles

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α-三氟甲基-α-羟基Weinreb酰胺的合成研究

康娟, 黄丹凤, 王克虎, 苏瀛鹏, 胡雨来, 常青

西北师范大学化学化工学院兰州 730070

收稿日期:2016-06-22 修回日期:2016-09-12 发布日期:2016-09-19
通讯作者: 黄丹凤, 胡雨来 E-mail:huyl@nwnu.edu.cn;huangdf@nwnu.edu.cn
基金资助:
国家自然科学基金（Nos. 21262031，21462037）资助项目.

Synthesis of α-Trifluoromethyl-α-hydroxyl Weinreb Amides

Kang Juan, Huang Danfeng, Wang Kehu, Su Yingpeng, Hu Yulai, Chang Qing

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2016-06-22 Revised:2016-09-12 Published:2016-09-19
Supported by:
Project supported by the National Natural Science Foundation of China(Nos. 21262031, 21462037).

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Kang Juan, Huang Danfeng, Wang Kehu, Su Yingpeng, Hu Yulai, Chang Qing. Synthesis of α-Trifluoromethyl-α-hydroxyl Weinreb Amides[J]. Chin. J. Org. Chem., 2017, 37(1): 103-109.

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[1] Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[2] Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C. D.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[3] Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Hong Kong, 2009.
[4] Cametti, M.; Crousse, B.; Metrangolo, P.; Milani, R.; Resnati, G. Chem. Soc. Rev. 2012, 41, 31.
[5] Littich R.; Scott, P. J. H. Angew. Chem., Int. Ed. 2012, 51, 1106.
[6] Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
[7] Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683.
[8] Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
[9] Alonso, C.; Marigorta, E. M.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847
[10] Nahm S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
[11] Zhao, W.; Liu, W. Chin. J. Org. Chem. 2015, 35, 55(in Chinese).(赵蔚, 刘伟, 有机化学, 2015, 35, 55.)
[12] Singh, J.; Satyamurthi, N.; Aidhen, I. S. J. Prakt. Chem./Chem-Ztg. 2000, 342, 340.
[13] Sibi, M. P. Org. Prep. Proced. Int, 1993, 25, 15.
[14] Pérez, M.; Pozo, C. D.; Reyes, F.; Rodríguez, A.; Francesch, A.; Echavarren, A. M.; Cuevas, C. Angew. Chem., Int. Ed. 2004, 43, 1724.
[15] Lygo, B.; Bhatias, M.; Cooke, J. W. B.; Hirst, D. J. Tetrahedron Lett. 2003, 44, 2529.
[16] Dias, L. C.; Sousa, M. A. D. Tetrahedron Lett. 2003, 44, 5625.
[17] Shimizu, T.; Kusada, J.; Ishiyama, H.; Nakata, T. Tetrahedron Lett. 2003, 44, 4965.
[18] Taillier, C.; Bellosta, V.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2145.
[19] Murphy, J. A.; Commeureuc, A. G. J.; Snaddon, T. N.; McGuire, T. M.; Khan, T. A.; Hisler, K.; Dewis, M. L.; Carling, R. Org. Lett. 2005, 7, 1427.
[20] Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry:Principles and Commercial Applications, Plenum, New York, 1994, p. 57.
[21] Quan, F.; Huang, D.; Xu, C.; Zhang, Z.; Niu, T.; Feng, H.; Cu, L.; HU, Y. Chin. J. Org. Chem. 2009, 29, 450(in Chinese).(权锋, 黄丹凤, 徐长明, 张正臣, 牛腾, 冯惠娟, 徐雷云, 胡雨来, 有机化学, 2009, 29, 450.)
[22] Wang, F.; Lu, A.; Huang, D.; Su, Y.; Xia, X.; Xu, Y.; Wang, K.-H.; Hu, Y. Chin. J. Org. Chem. 2015, 35, 1046(in Chinese).(王凤娇, 陆爱玲, 黄丹凤, 苏瀛鹏, 夏晓文, 徐艳丽, 王克虎, 胡雨来, 有机化学, 2015, 35, 1046.)
[23] Ma, l.; Lü, W.; Huang, D.; Niu, T.; Su, Y.; Wang, K.-H.; Hu, Y. Chin. J. Org. Chem. 2014, 34, 962(in Chinese).(马丽芳, 吕文贤, 黄丹凤, 牛腾, 苏瀛鹏, 王克虎, 胡雨来, 有机化学, 2014, 34, 962.)
[24] Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393.
[25] Stahly, G. P.; Bell, D. R. J. Org. Chem. 1989, 54, 2873.
[26] Singh, R. P.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579.
[27] Sibi, M. P. Org. Prep. Proc. Int. 1993, 25, 15.

α-三氟甲基-α-羟基Weinreb酰胺的合成研究

Synthesis of α-Trifluoromethyl-α-hydroxyl Weinreb Amides

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