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2019 , Vol. 39 >Issue 3: 754 - 760

DOI: https://doi.org/10.6023/cjoc201808027

研究论文

铑/锌共催化苯酚对氧杂苯并降冰片烯的不对称开环反应研究

  • 和振秀 ,
  • 周永云 ,
  • 孙蔚青 ,
  • 樊瑞峰 ,
  • 沈国礼 ,
  • 樊保敏
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  • a 云南民族大学 云南民族大学-香港浸会大学传统天然药物研发联合实验室 昆明 650500;
    b 云南民族大学 民族药资源化学国家民委-教育部重点实验室 昆明 650500

收稿日期: 2018-08-23

  修回日期: 2018-10-09

  网络出版日期: 2018-11-12

基金资助

国家自然科学基金（No.21572198）和云南省应用基础研究计划重点（No.2017FA004）资助项目.

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Asymmetric Ring Opening Reaction of Oxabenzonorbornadienes with Phenols Promoted by Rhodium/Zinc Complexes

  • He Zhenxiu ,
  • Zhou Yongyun ,
  • Sun Weiqing ,
  • Fan Ruifeng ,
  • Shen Guol ,
  • Fan Baomin
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  • a Yunnan Minzu University-Hong Kong Baptist University Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500;
    b Key Laboratory of Chemistry in Ethnic Medicinal Resources, Yunnan Minzu University, Kunming 650500

Received date: 2018-08-23

  Revised date: 2018-10-09

  Online published: 2018-11-12

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572198) and the Applied Basic Research Project of Yunnan Province (No. 2017FA004).

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摘要

通过研究发现[Rh（COD）Cl]2/ZnI2/（2R，4R）-（+）-2，4-bis（diphenylphosphino）pentane作为共催化体系，能有效地催化酚类亲核试剂对氧杂苯并降冰片烯的不对称亲核开环反应，获得较好的收率和良好的对映选择性.在优化后的反应条件下，该共催化体系具有良好的催化活性和底物适应能力，能够实现各种取代的酚类亲核试剂对氧杂苯并降冰片烯的不对称开环，高效而又经济地合成不同取代的含手性四氢萘结构单元的化合物.

关键词： 铑; 氧杂苯并降冰片烯; 共催化; 不对称开环反应; 路易斯酸

本文引用格式

和振秀 , 周永云 , 孙蔚青 , 樊瑞峰 , 沈国礼 , 樊保敏 . 铑/锌共催化苯酚对氧杂苯并降冰片烯的不对称开环反应研究[J]. 有机化学, 2019 , 39(3) : 754 -760 . DOI: 10.6023/cjoc201808027

Abstract

The complex of[Rh(COD) Cl]2 and 2R,4R) -(+) -2,4-bis(diphenylphosphino) pentane was used as an effective catalyst for the asymmetric ring opening reaction of oxabenzonorbornadienes with various phenols by employing ZnI2 as the activator. Under the optimized reaction conditions, high enantioselectivities with good yields could be obtained from a wide scope of oxabenzonorbornadienes and phenols.

Key words： rhodium; oxabenzonorbornadienes; Co-catalysis; symmetric ring opening reaction; Lewis acid

参考文献

[1] (a) Jeffs, P. W.; Lynn, D. G. J. Org. Chem. 1975, 40, 2958.
(b) Okuno, T.; Natsume, I.; Sawai, K.; Sawamura, K.; Furusaki, A.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 5653.
(c) Snyder, S. E.; Aviles-Garay, F. A.; Chakraborti, R.; Nichols, D. E.; Watts, V. J.; Mailman, R. B. J. Med. Chem. 1995, 38, 2395.
(d) Hsieh, T. J.; Chang, F. R.; Chia, Y. C.; Chen, C. Y.; Lin, H. C.; Chiu, H. F.; Wu, Y. C. J. Nat. Prod. 2001, 64, 1157.
(e) Idris, A.; Tantry, M. A.; Ganai, B. A.; Kamili, A. N.; Williamson, J. S. Phytochem. Lett. 2015, 11, 264.
[2] (a) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
(b) Rayabarapu, D. K.; Cheng, C. H. Acc. Chem. Res. 2007, 40, 971.
[3] (a) Yang, D.-Q.; Han, Y.-F. Chin. J. Org. Chem. 2006, 26, 1613(in Chinese). (杨定乔, 韩英锋, 有机化学, 2006, 26, 1613.)
(b) Cho, Y. H.; Tseng, N. W.; Senboku, H.; Lautens, M. Synthesis 2008, 2467.
(c) Dockendorff, C.; Jin, S. J.; Olsen, M.; Lautens, M.; Coupal, M.; Hodzic, L.; Spear, N.; Payza, K.; Walpole, C.; Tomaszewski, M. J. Bioorg. Med. Chem. Lett. 2009, 19, 1228.
(d) Liébert, C.; Brinks, M. K.; Capacci, A. G.; Fleming, M. J.; Lautens, M. Org. Lett. 2011, 13, 3000.
[4] (a) Lautens, M.; Fang, Y. Q. Org. Lett. 2003, 5, 3679.
(b) Lautens, M.; Fagnou, K.; Taylor, M. Org. Lett. 2000, 2, 1677.
[5] (a) Fagnou, M. K.; Taylor, M.; Rovis, T. J. Organomet. Chem. 2001, 624, 259.
(b) Tsui, G. C.; Dougan, P.; Lautens, M. Org. Lett. 2013, 15, 2652.
[6] (a) Lautens, M.; Fagnou, K.; Rovis, T. J. Am. Chem. Soc. 2000, 122, 5650.
(b) Lautens, M.; Fagnou, K. J. Am. Chem. Soc. 2001, 123, 7170.
(c) Lautens, M.; Fagnou, K.; Yang, D. Q. J. Am. Chem. Soc. 2003, 125, 14884.
(d) Cho, Y. H.; Zunic, V.; Senboku, H.; Olsen, M.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 6837.
[7] Leong, P.; Lautens, M. J. Org. Chem. 2004, 69, 2194.
[8] Lautens, M.; Fagnou, K. Tetrahedron 2001, 57, 5067.
[9] Tsui, G. C.; Lautens, M. Angew. Chem. Int. Ed. 2012, 51, 1.
[10] (a) Tsui, G. C.; Tsoung, J.; Dougan, P.; Lautens, M. Org. Lett. 2012, 14, 5542.
(b) Murakami, M.; Igawa, H. Chem. Commun. 2002, 4, 390.
(c) Preetz, A.; Kohrt, C.; Drexler, H.; Torrens, A.; Buschmann, H.; Lopez, M.; Heller, D. Adv. Synth. Catal. 2010, 352, 2073.
[11] (a) Yang, D.-Q.; Long, Y.-H.; Wang, H.; Zhang, Z.-M. Org. Lett. 2008, 10, 4723.
(b) Yang, D.-Q.; Long, Y.-H.; Zhang, J.-F.; Zeng, H.-P.; Wang, S.-Y.; Li, C.-R. Organometallics 2010, 29, 3477.
(c) Cheng, H.-C.; Yang, D.-Q. J. Org. Chem. 2012, 77, 9756.
(d) Long, Y.-H.; Wang, W.-L.; Yang, D.-Q.; Jiang, H.; Chen, K.-X.; Fang, Y.-L. Mol. Diversity 2014, 18, 101.
[12] Luo, R.-S.; Liao, J.-H.; Xie, L.; Tang, W.-J.; Chan, A. S. C. Chem. Commun. 2013, 49, 9959.
[13] (a) Li, S.-F.; Chen, H.-L.; Yang, Q.-J.; Yu, L.; Fan, C.-L.; Zhou, Y.-Y.; Wang, J.; Fan, B.-M. Asian J. Org. Chem. 2013, 2, 494.
(b) Yu, L.; Zhou, Y.-Y.; Xu, X.; Li, S.-F.; Xu, J.-B.; Fan, B.-M.; Lin, C.-Y.; Bian, Z.-X.; Chan, A. S. C. Tetrahedron Lett. 2014, 55, 6315.
(c) Lu, Z.-W.; Wang, J., Han, B.-Q.; Li, S.-F.; Zhou, Y.-Y.; Fan, B.-M. Adv. Synth. Catal. 2015, 357, 3121.
(d) Zeng, C. Y.; Yang, F.; Chen, J. C.; Wang, J.; Fan, B. M. Org. Biomol. Chem. 2015, 13, 8425.
(e) Zhou, Y.-Y.; Lu, Z.-W.; Han, B.-Q.; Zeng, C. Y.; Zhang, Z.-H.; Fan, B.-M. Tetrahedron:Asymmetry 2015, 26, 1354.
(f) Li, S.-F.; Xu, J.-B.; Fan, B.-M.; Lu, Z.-W.; Zeng, C.-Y.; Bian, Z.-X.; Zhou, Y.-Y.; Wang, J. Chem.-Eur. J. 2015, 21, 9003.
(g) Xu, X.; Chen, J.-C.; He, Z.-X.; Zhou, Y.-Y.; Fan, B.-M. Org. Biomol. Chem. 2016, 14, 2480.
(h) Zhou, Y.-Y.; Gu, C.-P.; Chen, J.-C.; Zhu, M.-N.; Yang, F.; Jianbin Xu, J.-B.; Fan, B.-M. Adv. Synth. Catal. 2016, 358, 3167.
(i) He, X.-B.; Chen, J.-C.; Xu, X.; Yang, F.; Gu, C.-P.; Zhou, Y.-Y.; Fan, B.-M. Tetrahedron:Asymmetry 2017, 28, 62.

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