Application of Chiral Anion Metathesis Strategy in Asymmetric Transfer Hydrogenation of Isoquinolines

doi:10.6023/A14050391

Acta Chimica Sinica ›› 2014, Vol. 72 ›› Issue (7): 820-824.DOI: 10.6023/A14050391 Previous Articles Next Articles

Special Issue: 不对称催化与合成

Communication

基于手性负离子置换策略的异喹啉不对称转移氢化研究

时磊^a,b, 姬悦^a, 黄文学^a, 周永贵^a

a 中国科学院大连化学物理研究所大连 116023;
b 大连理工大学精细化工国家重点实验室大连 116024

投稿日期:2014-05-19 发布日期:2014-06-17
通讯作者: 时磊, 周永贵 E-mail:shileichem@dicp.ac.cn;ygzhou@dicp.ac.cn
基金资助:
项目受国家自然科学基金青年科学基金项目（No.21202162）和大连理工大学精细化工国家重点实验室开放课题基金（No.KF1110）资助.

Application of Chiral Anion Metathesis Strategy in Asymmetric Transfer Hydrogenation of Isoquinolines

Shi LeiJi^a,b, Yue Huang^a, Wen xue^a, Zhou Yonggui^a

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China;
b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Received:2014-05-19 Published:2014-06-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21202162) and the State Key Laboratory of Fine Chemicals (No. KF1110).

1. Application of Chiral Anion Metathesis Strategy in Asymmetric Transfer Hydrogenation of Isoquinolines.PDF(2338KB)

Abstract

Asymmetric hydrogenation of N-hetero aromatics offers a very straightforward and efficient method to obtain the corresponding chiral N-hetero cyclic saturated or partially saturated compounds. As one of the most challenging substrates, asymmetric hydrogenation of isoquinolines has met with limited success probably because of lower reactivity and the catalyst deactivation resulted from strong coordination. Considering the prevalence of the chiral 1,2,3,4-tetrahydroisoquinoline motif in natural alkaloids and drug molecules, the development of new catalyst system for asymmetric hydrogenation of isoquinolines is highly desirable and significant. Herein, a novel chiral anion metathesis strategy successfully applied for asymmetric transfer hydrogenation of isoquinolines is reported. N-Protected 1-substituted 1,2-dihydroisoquinolines were obtained with high yield and up to 79% ee in the presence of Hantzsch ester and chloroformate using chiral phosphoric acid as catalyst. The phosphate salt and the activated N-acyl isoquinolinium chloride undergo anion metathesis to form chiral contact ion pair, which leads to a highly enantioselective transfer hydrogenation of isoquinolines. After systematically investigating the effects of activating reagent, solvent, base, hydride donor and catalyst on this transfer hydrogenation reaction, the best result was achieved under the optimized condition as follows: 5 mol% H8-BINOL-derived chiral phosphoric acid as catalyst, 1.2 equivalent 2,2,2-trichloroethyl chloroformate as activator, 1.5 equivalent dimethyl 2,6-diethyl-1,4-dihydropyridine-3,5- dicarboxylate as hydride donor, 1.5 equivalent sodium carbonate as base and cyclohexane as solvent. The reaction is tolerant toward a broad range of aryl or alkyl 1-substituted isoquinoline substrates. This methodology represents one of the rare examples of asymmetric hydrogenation of this challenging substrate. The utilizing of chiral anion metathesis strategy could enable chiral phosphoric acid to catalyze more asymmetric transformation process and further researching is ongoing in our laboratory.

Key words: chiral phosphoric acid, chiral anion metathesis, transfer hydrogenation, isoquinolines

Cite this article

Shi LeiJi, Yue Huang, Wen xue, Zhou Yonggui. Application of Chiral Anion Metathesis Strategy in Asymmetric Transfer Hydrogenation of Isoquinolines[J]. Acta Chimica Sinica, 2014, 72(7): 820-824.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.

[2] Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.

[3] Rueping, M.; Sugiono, E.; Azap, C. Angew. Chem. Int. Ed. 2006,

[4] Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem. Int. Ed. 2006, 45, 4796.

[5] Rueping, M.; Azap, C. Angew. Chem. Int. Ed. 2006, 45, 7832.

[6] Liu, H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. Org. Lett. 2006, 8, 6023.

[7] Lv, J.; Zhong, X.-R.; Cheng, J.-P.; Luo, S.-Z. Acta Chim. Sinica 2012, 70, 1518. (吕健, 钟兴仁, 程津培, 罗三中, 化学学报, 2012, 70, 1518.)

[8] Huang, J.-Z.; Luo, S.-W.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 879. (黄建洲, 罗时玮, 龚流柱, 化学学报, 2013, 71, 879.)

[9] Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781.

[10] Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem. Int. Ed. 2005, 44, 7424.

[11] Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 6751.

[12] Li, G.-L.; Liang, Y.-X.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 5830.

[13] Rueping, M.; Sugiono, E.; Schoepke, F.-R. Synlett 2010, 852.

[14] Kang, Q.; Zhao, Z.-A.; You, S.-L. Org. Lett. 2008, 10, 2031.

[15] Wang, D.; Hou, C.-J.; Chen, L.-F.; Liu, X.-N.; An, Q.-D.; Hu, X.-P. Chin. J. Org. Chem. 2013, 33, 1355. (王东, 侯传金, 陈丽凤, 刘小宁, 安庆大, 胡向平, 有机化学, 2013, 33, 1355.)

[16] Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q.-L. Angew. Chem. Int. Ed. 2007, 46, 5565.

[17] Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484.

[18] Sheng, Y.-F.; Zhang, A.-J.; Zheng, X.-J.; You, S.-L. Chin. J. Org. Chem. 2008, 28, 605. (盛益飞, 张安将, 郑晓建, 游书力, 有机化学, 2008, 28, 605.)

[19] Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292.

[20] He, Z.-R.; Huang, Y.-Y.; Verpoort, F. Acta Chim. Sinica 2013, 71, 700. (何展荣, 黄毅勇, Verpoort Francis, 化学学报, 2013, 71, 700.)

[21] Xu, S.; Wang, Z.; Zhang, X.; Zhang, X.; Ding, K. Angew. Chem. Int. Ed. 2008, 47, 2840.

[22] Su, Y.-J.; Shi, F.-Q. Chin. J. Org. Chem. 2010, 30, 486. (苏亚军, 史福强, 有机化学, 2010, 30, 486.)

[23] Wu, X.; Li, M.-L.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 1091. (吴祥, 李明丽, 龚流柱, 化学学报, 2013, 71, 1091.)

[24] Lv, J.; Luo, S.-Z. Chem. Commun. 2013, 49, 847.

[25] Xu, B.; Zhu, S.-F.; Zhang, Z.-C.; Yu, Z.-X.; Ma, Y.; Zhou, Q.-L. Chem. Sci. 2014, 5, 1442.

[26] Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.; Doyle, M. P.; Hu, W.-H. Nature Chemistry 2012, 4, 733.

[27] Qiu, H.; Zhang, D.; Liu, S.-Y.; Qiu, L.; Zhou, J.; Qian, Y.; Zhai, C.-W.; Hu, W.-H. Acta Chim. Sinica 2012, 70, 2484. (邱晃, 张丹, 刘顺英, 邱林, 周俊, 钱宇, 翟昌伟, 胡文浩, 化学学报, 2012, 70, 2484.)

[28] Mahlau, M.; List, B. Angew. Chem. Int. Ed. 2013, 52, 518.

[29] Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science 2011, 334, 1681.

[30] Wang, Y.-M.; Wu, J.; Hoong, C.; Rauniyar, V.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 12928.

[31] Phipps, R. J.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 1268.

[32] Lackner, A. D.; Samant, A. V.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 14090.

[33] Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498.

[34] Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 3683.

[35] Glorius, F. Org. Biomol. Chem. 2005, 3, 4171.

[36] Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Chin. J. Org. Chem. 2005, 25, 634. (卢胜梅, 韩秀文, 周永贵, 有机化学, 2005, 25, 634.)

[37] Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357.

[38] Kuwano, R. Heterocycles 2008, 76, 909.

[39] Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557.

[40] Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427. (谢建华, 周其林, 化学学报, 2012, 70, 1427.)

[41] He, Y.-M.; Song, F.-T.; Fan, Q.-H. Top. Curr. Chem. 2014, 343, 145.

[42] Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.

[43] Zhou, H.-F.; Li, Z.-W.; Wang, Z.-J.; Wang, T.-L.; Xu, L.-J.; He, Y.-M.; Fan, Q.-H.; Pan, J.; Gu, L.-Q.; Chan, A. S. C. Angew. Chem. Int. Ed. 2008, 47, 8464.

[44] Wang, T.-L.; Zhuo, L.-G.; Li, Z.-W.; Chen, F.; Ding, Z.-Y.; He, Y.-M.; Fan, Q.-H.; Xiang, J.-F.; Yu, Z.-X.; Chan, A. S. C. J. Am. Chem. Soc. 2011, 133, 9878.

[45] Lei, A.; Chen, M.; He, M.; Zhang, X. Eur. J. Org. Chem. 2006, 4343.

[46] Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.

[47] Guo, Q.-S.; Du, D. M.; Xu, J.-X. Angew. Chem. Int. Ed. 2008, 47, 759.

[48] Rueping, M.; Tato, F.; Schoepke, F. R. Chem. Eur. J. 2010, 16, 2688.

[49] Rueping, M.; Antonchick, A. P. Angew. Chem. Int. Ed. 2007, 46, 4562.

[50] Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem. Int. Ed. 2006, 45, 2260.

[51] Shi, L.; Ye, Z.-S.; Cao, L.-L.; Guo, R.-N.; Hu, Y.; Zhou, Y.-G. Angew. Chem. Int. Ed. 2012, 51, 8286.

[52] Ye, Z.-S.; Guo, R.-N.; Cai, X.-F.; Chen, M.-W.; Shi, L.; Zhou, Y.-G. Angew. Chem. Int. Ed. 2013, 52, 3685.

[53] Iimuro, A.; Yamaji, K.; Kandula, S.; Nagano, T.; Kita, Y.; Mashima, K. Angew. Chem. Int. Ed. 2013, 52, 2046.

[54] Guo, R.-N.; Cai, X.-F.; Shi, L.; Ye, Z.-S.; Chen, M.-W.; Zhou, Y.-G. Chem. Commun. 2013, 49, 8537.

基于手性负离子置换策略的异喹啉不对称转移氢化研究

Application of Chiral Anion Metathesis Strategy in Asymmetric Transfer Hydrogenation of Isoquinolines

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 10

Recommended Articles

Metrics

Comments

[1]	Zhou Xiao-Le, Su Yong-Liang, Wang Pu-Sheng, Gong Liu-Zhu. Asymmetric Allylic C-H Alkylation of 1,4-Dienes with Aldehydes [J]. Acta Chim. Sinica, 2018, 76(11): 857-861.
[2]	Li Sujia, Lü Jian, Luo Sanzhong. Enantioselective Indium(I)/Chiral Phosphoric Acid-catalyzed[4+2] Cycloaddition of Simple Olefin and β,γ-Unsaturated α-Keto Esters [J]. Acta Chim. Sinica, 2018, 76(11): 869-873.
[3]	Li Xue-Fei, Lin Jin-Shun, Wang Jian, Li Zhong-Liang, Gu Qiang-Shuai, Liu Xin-Yuan. Cu/Chiral Phosphoric Acid-Catalyzed Asymmetric Radical-Initiated Aminoarylation of Alkenes [J]. Acta Chimica Sinica, 2018, 76(11): 878-882.
[4]	Zhang Zi-Jing, Tao Zhong-Lin, Arafate Adele, Gong Liu-Zhu. Asymmetric Carbonyl Allylation of Aldehydes with Allylic Alcohols under the Sequential Catalysis of Palladium Complex and Chiral Phosphoric Acid [J]. Acta Chim. Sinica, 2017, 75(12): 1196-1201.
[5]	Duan Dehe, Yin Qin, Wang Shouguo, Gu Qing, You Shuli. Chiral Phosphoric Acid-Catalyzed Asymmetric Cascade Reaction of C(3) Substituted Indoles and Methyl Vinyl Ketone [J]. Acta Chim. Sinica, 2014, 72(9): 1001-1004.
[6]	Yan Long, Pang Huan, Huang Yaobing, Fu Yao. Supported Pd Catalysts for the C—O Cleavage of the Lignin Derived Model Dimers through Intramolecular Hydrogenolysis Reaction [J]. Acta Chimica Sinica, 2014, 72(9): 1005-1011.
[7]	Ji Yigang, Wu Lei, Fan Qinghua. Recent Progress of Metal/Metal Oxide Nanoparticles for Asymmetric Hydrogenation and Transfer Hydrogenation [J]. Acta Chimica Sinica, 2014, 72(7): 798-808.
[8]	Wu Xiang, Li Mingli, Gong Liuzhu. Asymmetric Relay Catalysis Reaction Consisting of Metal Complex and Chiral Phosphoric Acids [J]. Acta Chimica Sinica, 2013, 71(08): 1091-1100.
[9]	Huang Jianzhou, Luo Shiwei, Gong Liuzhu. Chiral Brønsted Acid Catalyzed Stereoselective [3+3] Cycloaddition Reaction of Azomethine Ylide to Vinylimine Intermediates: Constructing Fully Functionalized Chiral Tetrahydro-β-Carboline [J]. Acta Chimica Sinica, 2013, 71(06): 879-883.
[10]	CHEN Jian-Shan, CHEN Ling-Ling, XING Yan, CHEN Gui, SHEN Wei-Yi, DONG Zhen-Rong, LI Yan-Yun, GAO Jing-Xing. Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems [J]. Acta Chimica Sinica, 2004, 62(18): 1745-1750.