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

doi:10.6023/cjoc201808027

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 754-760.DOI: 10.6023/cjoc201808027 Previous Articles Next Articles

Articles

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^a, 周永云^a, 孙蔚青^a, 樊瑞峰^b, 沈国礼^a, 樊保敏^a,b

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 发布日期:2018-11-12
通讯作者: 周永云, 樊保敏 E-mail:zhouyongyundf@163.com;adams.bmf@hotmail.com
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.

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

He Zhenxiu^a, Zhou Yongyun^a, Sun Weiqing^a, Fan Ruifeng^b, Shen Guol^a, Fan Baomin^a,b

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:2018-08-23 Revised:2018-10-09 Published:2018-11-12
Contact: 10.6023/cjoc201808027 E-mail:zhouyongyundf@163.com;adams.bmf@hotmail.com
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).

1. Asymmetric Ring Opening Reaction of Oxabenzonorbornadienes with Phenols Promoted by Rhodium/Zinc Complexes.PDF(3259KB)

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

Cite this article

He Zhenxiu, Zhou Yongyun, Sun Weiqing, Fan Ruifeng, Shen Guol, Fan Baomin. Asymmetric Ring Opening Reaction of Oxabenzonorbornadienes with Phenols Promoted by Rhodium/Zinc Complexes[J]. Chin. J. Org. Chem., 2019, 39(3): 754-760.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

[1]	Si Wen, Yuhao Ding, Qingyu Tian, Jin Ge, Guolin Cheng. Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 291-300.
[2]	Zujia Chen, Shiwei Yu, Yongjun Zhou, Huanqing Li, Qiwen Qiu, Miaoxin Li, Zhaoyang Wang. Application of BF₃•OEt₂ in Organic Synthesis as a Catalyst or Synthon [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3107-3118.
[3]	Yanbo Zhang, Meng Sun. Rh(III)-Catalyzed C(7)—H Formylmethylation of Indoline with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2905-2912.
[4]	Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681.
[5]	Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 961-973.
[6]	Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui. Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1187-1196.
[7]	Yiling Zhao, Zhikang Chen, Lei Li, Conglei Liu, Hongping Zhu. Silylene/Organoaluminum Lewis Pair System and the Initiation Property for Polymerization of (Meth)acrylates [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3590-3597.
[8]	Xiangqing Feng, Haifeng Du. B(C₆F₅)₃-Catalyzed Silylation of Unsaturated Hydrocarbons [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3544-3557.
[9]	Dan Ba, Guolin Cheng. Blue Light Induced Insertion of Carbene into C(CO)—C Bonds of 1,3-Diones [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2888-2897.
[10]	Min Hua, Yangxing Sun, Xueqing Zhang, Hui Yao, Nianyu Huang. Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2140-2154.
[11]	Xuerong Chen, Liang Qi, Jinpei Huang, Weiwei Zhu, Yifeng Zhou. Lewis Acid Promoted Intramolecular Nucleophilic Heterocyclization of Unsaturated Amides for the Synthesis of 2-Oxazolines and Their Applications in Imaging of Living Cells [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2155-2163.
[12]	Xiaojie Liu, Biping Xu, Weiping Su. Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2184-2191.
[13]	Gaoxu Han, Hongtao Xu, Wei Hou. Rhodium(III) Catalyzed C(sp³)—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 391-423.
[14]	Fangjie Li, Bin Lu, Yang Liu, Xiaoming Wang. Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3390-3397.
[15]	Xiuliang Cheng, Dong Li, Boxuan Yang, Yumei Lin, Lei Gong. Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3335-3350.

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

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments