Enantioselective Hydrosilylation of N-Aryl Diaryl Ketimines

doi:10.6023/cjoc201512049

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1895-1906.DOI: 10.6023/cjoc201512049 Previous Articles Next Articles

ARTICLE

二芳基甲酮亚胺的不对称催化氢化硅烷化反应研究

扈晓艳^a,b, 胡方芝^a,b, 张敏敏^a,b, 廖益均^a,b, 徐小英^a, 袁伟成^a, 张晓梅^a

a 中国科学院成都有机化学研究所成都 610041;
b 中国科学院大学北京 100049

收稿日期:2015-12-30 修回日期:2016-04-02 发布日期:2016-04-07
通讯作者: 张晓梅 E-mail:xmzhang@cioc.ac.cn
基金资助:
国家自然科学基金（No. 21172217）资助项目.

Enantioselective Hydrosilylation of N-Aryl Diaryl Ketimines

Hu Xiaoyan^a,b, Hu Fangzhi^a,b, Zhang Minmin^a,b, Liao Yijun^a,b, Xu Xiaoying^a, Yuan Weicheng^a, Zhang Xiaomei^a

a Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041;
b University of Chinese Academy of Sciences, Beijing, 100049

Received:2015-12-30 Revised:2016-04-02 Published:2016-04-07
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172217).

1. Enantioselective Hydrosilylation of N-Aryl Diaryl Ketimines.PDF(7836KB)

Abstract

Lewis base catalyzed enantioselective hydrosilylation of non-ortho-substituted N-aryl diaryl ketimines was realized. In the presence of 20 mol% of the optimal catalyst, the reactions provided a series of (diarylmethyl)amines with high yields (up to 97%) in moderate to good enantioselectivities (up to 89% ee). The absolute configuration of one product was determined by X-ray crystallographic analysis.

Key words: diarylmethylamines, diaryl ketimines, chiral Lewis base, hydrosilylation

Cite this article

Hu Xiaoyan, Hu Fangzhi, Zhang Minmin, Liao Yijun, Xu Xiaoying, Yuan Weicheng, Zhang Xiaomei. Enantioselective Hydrosilylation of N-Aryl Diaryl Ketimines[J]. Chin. J. Org. Chem., 2016, 36(8): 1895-1906.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Spencer, C. M.; Faulds, D.; Peters, D. H. Drugs 1993, 46, 1055.
(b) Bishop, M. J.; Mcnutt, R. W. Bioorg. Med. Chem. Lett. 1995, 5, 1311.
(c) Bilsky, E. J.; Calderon, S. N.; Wang, T.; Bernstein, R. N.; Davis, P.; Hruby, V. J.; Mcnutt, R. W.; Rothman, R. B.; Rice, K. C.; Porreca, F. J. Pharmacol. Exp. Ther. 1995, 273, 359.
(d) Sakurai, S.; Ogawa, N.; Suzuki, T.; Kato, K.; Ohashi, T.; Yasuda, S.; Kato, H.; Ito, Y. Chem. Pharm. Bull. 1996, 44, 765.
(e) Plobeck, N.; Delorme, D.; Wei, Z. Y.; Yang, H.; Zhou, F.; Schwarz, P.; Gawell, L.; Gagnon, H.; Pelcman, B.; Schmidt, R.; Yue, S. Y.; Walpole, C.; Brown, W.; Zhou, E.; Labarre, M.; Payza, K.; St-Onge, S.; Kamassah, A.; Morin, P. E.; Projean, D.; Ducharme, J.; Roberts, E. J. Med. Chem. 2000, 43, 3878.
(f) Gillard, M.; Van Der Perren, C.; Moguilevsky, N.; Massingham, R.; Chatelain, P. Mol. Pharmacol. 2002, 61, 391.
(g) Cetinkaya, Y.; Gocer, H.; Goksu, S.; Gulcin, I. J. Enzyme Inhib. Med. Chem. 2014, 29, 168.
[2] For a review, see: Schmidt, F.; Stemmler, R. T.; Rudolph, J.; Bolm, C. Chem. Soc. Rev. 2006, 35, 454.
[3] (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681.
(b) Delorme, D.; Berthelette, C.; Lavoie, R.; Roberts, E. Tetrahedron: Asymmetry 1998, 9, 3963.
(c) Pflum, D. A.; Krishnamurthy, D.; Han, Z. X.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923.
(d) Plobeck, N.; Powell, D. Tetrahedron: Asymmetry 2002, 13, 303.
(e) Han, Z. X.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Pflum, D. A.; Senanayake, C. H. Tetrahedron Lett. 2003, 44, 4195.
(f) Cabello, N.; Kizirian, J. C.; Alexakis, A. Tetrahedron Lett. 2004, 45, 4639.
(g) Weix, D. J.; Shi, Y. L.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092.
(h) Bolshan, Y.; Batey, R. A. Org. Lett. 2005, 7, 1481.
(i) Boebel, T. A.; Hartwig, J. F. Tetrahedron 2008, 64, 6824.
(j) Haurena, C.; LeGall, E.; Sengmany, S.; Martens, T. Tetrahedron 2010, 66, 9902.
(k) Han, Z. X.; Busch, R.; Fandrick, K. R.; Meyer, A.; Xu, Y. B.; Krishnamurthy, D. K.; Senanayake, C. H. Tetrahedron 2011, 67, 7035.
[4] (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976.
(b) Hermanns, N.; Dahmen, S.; Bolm, C.; Brase, S. Angew. Chem., Int. Ed. 2002, 41, 3692.
(c) Kuriyama, M.; Soeta, T.; Hao, X. Y.; Chen, O.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128.
(d) Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584.
(e) Hayashi, T.; Kawai, M.; Tokunaga, N. Angew. Chem., Int. Ed. 2004, 43, 6125. .
(f) Otomaru, Y.; Tokunaga, N.; Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 307.
(g) Cabello, N.; Kizirian, J. C.; Gille, S.; Alexakis, A.; Bernardinelli, G.; Pinchard, L.; Caille, J. C. Eur. J. Org. Chem. 2005, 4835.
(h) Jagt, R. B. C.; Toullec, P. Y.; Geerdink, D.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. D. J. Angew. Chem., Int. Ed. 2006, 45, 2789.
(i) Duan, H. F.; Jia, Y. X.; Wang, L. X.; Zhou, Q. L. Org. Lett. 2006, 8, 2567-2569.
(j) Wang, Z. Q.; Feng, C. G.; Xu, M. H.; Lin, G. Q. J. Am. Chem. Soc. 2007, 129, 5336.
(k) Clayden, J.; Dufour, J.; Grainger, D. M.; Helliwell, M. J. Am. Chem. Soc. 2007, 129, 7488.
(l) Nakagawa, H.; Rech, J. C.; Sindelar, R. W.; Ellman, J. A. Org. Lett. 2007, 9, 5155.
(m) Marelli, C.; Monti, C.; Gennari, C.; Piarulli, U. Synlett 2007, 2213.
(n) Okamoto, K.; Hayashi, T.; Rawal, V. H. Chem. Commun. 2009, 4815.
(o) Hao, X. Y.; Kuriyama, M.; Chen, Q.; Yamamoto, Y.; Yamada, K.; Tomioka, K. Org. Lett. 2009, 11, 4470.
(p) Shintani, R.; Takeda, M.; Tsuji, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 13168.
(q) Cao, Z. P.; Du, H. F. Org. Lett. 2010, 12, 2602.
(r) Shintani, R.; Soh, Y. T.; Hayashi, T. Org. Lett. 2010, 12, 4106.
(s) Shao, C.; Yu, H. J.; Wu, N. Y.; Feng, C. G.; Lin, G. Q. Org. Lett. 2010, 12, 3820.
(t) Wang, L.; Wang, Z. Q.; Xu, M. H.; Lin, G. Q. Synthesis 2010, 3263.
(u) Crampton, R.; Woodward, S.; Fox, M. Adv. Synth. Catal. 2011, 353, 903.
(v) Hao, X. Y.; Chen, Q.; Kuriyama, M.; Yamada, K.; Yamamoto, Y.; Tomioka, K. Catal. Sci. Technol. 2011, 1, 62.
(w) Shintani, R.; Narui, R.; Tsutsumi, Y.; Hayashi, S.; Hayashi, T. Chem. Commun. 2011, 47, 6123.
(x) Han, W. Y.; Wu, Z. J.; Zhang, X. M.; Yuan, W. C. Org. Lett. 2012, 14, 976.
(y) Han, W. Y.; Zuo, J.; Zhang, X. M.; Yuan, W. C. Tetrahedron 2013, 69, 537.
[5] (a) Malkov, A. V.; Vrankova, K.; Ston?ius, S.; Ko?ovsky, P. J. Org. Chem. 2009, 74, 5839.
(b) Hou, G. H.; Tao, R.; Sun, Y.; Zhang, X. M.; Gosselin, F. J. Am. Chem. Soc. 2010, 132, 2124.
(c) Nguyen, T. B.; Wang, Q.; Gueritte, F. Chem. Eur. J. 2011, 17, 9576.
(d) Thanh, B. N.; Bousserouel, H.; Wang, Q. A.; Gueritte, F. Adv. Synth. Catal. 2011, 353, 257.
(e) Amezquita-Valencia, M.; Cabrera, A. J. Mol. Catal. A: Chem. 2013, 366, 17.
(f) Hu, X. Y.; Zhang, M. M.; Shu, C.; Zhang, Y. H.; Liao, L. H.; Yuan, W. C.; Zhang, X. M. Adv. Synth. Catal. 2014, 356, 3539.
[6] Chu, L.; Wang, X. C.; Moore, C. E.; Rheingold, A. L.; Yu, J. Q. J. Am. Chem. Soc. 2013, 135, 16344.
[7] For some recent reviews, see: (a) Zhou, Q. L.; Xie, J. H. Top. Curr. Chem. 2014, 343, 75.
(b) Li, X. H.; Wu, P. Curr. Org. Chem. 2014, 18, 1242-1261.
(c) Ji, Y. G.; Wu, L.; Fan, Q. H. Acta Chim. Sinica 2014, 72, 798 (in Chinese).
(季益刚, 吴磊, 范青华, 化学学报, 2014, 72, 798.)
(d) He, Y. M.; Song, F. T.; Fan, Q. H. Top. Curr. Chem. 2014, 343, 145.
(e) Wang, D.; Hou, C. J.; Chen, L. F.; Liu, X. N.; An, Q. D.; Hu, X. P. Chin. J. Org. Chem. 2013, 33, 1355 (in Chinese).
(王东, 侯传金, 陈丽凤, 刘小宁, 安庆大, 胡向平, 有机化学, 2013, 33, 1355.)
(f) Chen, Q. A.; Ye, Z. S.; Duan, Y.; Zhou, Y. G. Chem. Soc. Rev. 2013, 42, 497.
(g) Etayo, P.; Vidal-Ferran, A. Chem. Soc. Rev. 2013, 42, 728.
(h) Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Soc. Rev. 2012, 41, 4126.
(i) Xie, J. H.; Zhou, Q. L. Acta Chim. Sinica 2012, 70, 1427 (in Chinese).
(谢建华, 周其林, 化学学报, 2012, 70, 1427.)
(j) Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753.
(k) Cheng, T. Y.; Zhao, Q. K.; Zhang, D. C.; Liu, G. H. Curr. Org. Chem. 2015, 19, 667.
(l) Foubelo, F.; Yus, M. Chem. Rec. 2015, 15, 907.
(m) Zheng, C.; You, S. L. Chem. Soc. Rev. 2012, 41, 2498.
(n) Robertson, A.; Matsumoto, T.; Ogo, S. Dalton Trans. 2011, 40, 10304.
(o) Tang, Y. F.; Deng, J. G. Prog. Chem. 2010, 22, 1242.
(p) Wang, Z. Y.; Jiang, Z. J. Asian J. Chem. 2010, 22, 4141.
(q) Jones, S.; Warner, C. J. A. Org. Biomol. Chem. 2012, 10, 2189.
(r) Weickgenannt, A.; Oestreich, M. ChemCatChem 2011, 3, 1527.
(s) Guizzetti, S.; Benaglia, M. Eur. J. Org. Chem. 2010, 5529.
[8] Zheng, H. J.; Deng, J. G.; Lin, W. Q.; Zhang, X. M. Tetrahedron Lett. 2007, 48, 7934.
[9] Jiang, Y.; Chen, X.; Zheng, Y. S.; Xue, Z. Y.; Shu, C.; Yuan, W. C.; Zhang, X. M. Angew. Chem., Int. Ed. 2011, 50, 7304.
[10] Chen, X.; Hu, X. Y.; Shu, C.; Zhang, Y. H.; Zheng, Y. S.; Jiang, Y.; Yuan, W. C.; Liu, B.; Zhang, X. M. Org. Biomol. Chem. 2013, 11, 3089.
[11] Xue, Z. Y.; Jiang, Y.; Yuan, W. C.; Zhang, X. M. Eur. J. Org. Chem. 2010, 616.
[12] Zheng, H. J.; Deng, J. G.; Lin, W. Q.; Zhang, X. M. Tetrahedron Lett. 2007, 48, 7934.
[13] CCDC 1038813 (for 2a) contains the supplementary crystallo graphic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc. cam. ac. uk/data_request/cif.
[14] Artico, M.; De Martino, G.; Pasquali, A. D.; Regina, G. L.; Silvestri, R.; Ragno, R.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Crespan, E.; Maga, G. J. Med. Chem. 2003, 46, 2482.
[15] Sato, M.; Nagashima, S.; Murakami, M.; Kaneko, C. Tetrahedron 1993, 49, 6575.

二芳基甲酮亚胺的不对称催化氢化硅烷化反应研究

Enantioselective Hydrosilylation of N-Aryl Diaryl Ketimines

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Zijie Song, Jun Liu, Ying Bai, Jiayun Li, Jiajian Peng. Progress in Catalysis Transformation of Carbon Dioxide through Hydrosilylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2068-2080.
[2]	Wei Sun, Shoufei Zhu. Hydrosilylation Reactions of Alkene with Tertiary Silanes Catalyzed by Iron-Series Metals [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3339-3351.
[3]	Jun Liu, Jiajian Peng, Ying Bai, Jiayun Li, Zijie Song, Peng Liu, Ting Ouyang, Huilin Lan. Progress in Photocatalytic Hydrosilylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3558-3568.
[4]	Xiangqing Feng, Haifeng Du. B(C₆F₅)₃-Catalyzed Silylation of Unsaturated Hydrocarbons [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3544-3557.
[5]	Peifeng Su, Jinyu Ni, Zhuofeng Ke. Recent Advances in Homogeneous Catalytic Systems for CO₂Hydrosilylation and Related Transformations [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3526-3543.
[6]	Fengjuan Chen, Luo Liu, Zilu Zhang, Wei Zeng. Recent Progress in Synthesis of Organosilanes Driven by Visible-Light [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3454-3469.
[7]	Xin Li, Qiuling Song. Chiral Borane-Catalyzed Enantioselective Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3143-3151.
[8]	Dai Zinan, Yu Zehao, Bai Ying, Li Jiayun, Peng Jiajian. Progress in Catalysis of Hydrosilylation by Cobalt Complexes [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1177-1187.
[9]	Wang Zichao, Xu Youjun, Shi Shiliang. Base-Promoted Rapid Hydrosilylation of Aldimine [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3463-3466.
[10]	Wang Qiaotian, Han Caifang, Feng Xiangqing, Du Haifeng. Chiral Spiro Dienes Derived Boranes for Asymmetric Hydrosilylation of Ketones [J]. Chin. J. Org. Chem., 2019, 39(8): 2257-2263.
[11]	Luan Huaxin, Sun Hongjian, Xue Benjing, Li Xiaoyan. Synthesis and Properties of a Se-Coordinated Hydrido Cobalt(III) Complex Supported by Trimethylphosphine [J]. Chin. J. Org. Chem., 2017, 37(6): 1392-1397.
[12]	Zhang Feng, Liu Xianghua, Liu Wei, Deng Guojun. Application of Pd-Monodentate Phosphorus Catalysts in the Asymmetric Hydrosilylation Reactions of Alkenes [J]. Chin. J. Org. Chem., 2017, 37(10): 2555-2568.
[13]	Xiao Jianjun, Qiu Zumin, He Weijuan, Du Chengcheng, Zhou Wei. Progress in Platinum Catalysts Supported by Inorganic Carriers for Hydrosilylation [J]. Chin. J. Org. Chem., 2016, 36(5): 987-999.
[14]	Qin Xiaofei, Liu Xiaoyan, Guo Caihong, Wu Haishun. Reaction Mechanisms of Carbonyl Compounds Hydrosilylation Catalyzed by Group VIII Transition Metal Complexes [J]. Chin. J. Org. Chem., 2016, 36(1): 60-71.
[15]	Xu Dapeng, Xiao Wenjun, Peng Jiajian, Li Jiayun, Bai Ying. Progress in Hydrosilylation Catalyzed with Iron Catalyst [J]. Chin. J. Org. Chem., 2014, 34(11): 2195-2201.