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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1353 - 1358

DOI: https://doi.org/10.6023/cjoc201205007

ACCOUNT

Study on the Highly Selective Asymmetric Hydrogenation of Polyfunctionalized Carbonyl Substrates

  • Ma Xin ,
  • Li Wanfang ,
  • Fan Weizheng ,
  • Tao Xiaoming ,
  • Li Xiaoming ,
  • Yao Ying ,
  • Zhu L黤eng ,
  • Chen Houhe ,
  • Xie Xiaomin ,
  • Zhang Zhaoguo
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  • a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240;
    b School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094;
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry,
    Chinese Academy of Sciences, Shanghai 200032

Received date: 2012-05-07

  Revised date: 2012-06-18

  Online published: 2012-06-20

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20872090, 21172146).

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Abstract

In this account, our recent progress in highly chemo- and stereo-selective asymmetric hydrogenation of some polyfunctionalized carbonyl substrates is briefly reviewed. The furtherance of the study in this field and their applications is prospected.

Key words： asymmetric hydrogenation; carbonyls; polyfunctionalized; chemoselectivity; enantioselectivity

Cite this article

Ma Xin , Li Wanfang , Fan Weizheng , Tao Xiaoming , Li Xiaoming , Yao Ying , Zhu L黤eng , Chen Houhe , Xie Xiaomin , Zhang Zhaoguo . Study on the Highly Selective Asymmetric Hydrogenation of Polyfunctionalized Carbonyl Substrates[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1353 -1358 . DOI: 10.6023/cjoc201205007

References

[1] (a) Kitamura, M.; Noyori, R. In Ruthenium in Organic Synthesis, Ed.: Murahashi, S.-I., Wiley-VCH, Weinheim, 2004, p. 3.(b) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994, p. 17.(c) de Vries, J. G.; Elsevier, C. J. The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, 2007.

[2] Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.

[3] Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.

[4] Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.

[5] Noyori, R. Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York, 1994.

[6] Sun, Y.; Wan, X.; Guo, M.; Wang, D.; Dong, X.; Pan, Y.; Zhang, Z. Tetrahedron: Asymmetry 2004, 15, 2185.

[7] (a) Sun, Y.; Wan, X.; Guo, M.; Wang, D.; Dong, X.; Pan, Y.; Zhang, Z. Tetrahedron: Asymmetry 2004, 15, 2185.(b) Wan, X.; Sun, Y.; Luo, Y.; Li, D.; Zhang, Z. J. Org. Chem. 2005, 70, 1070.(c) Sun, Y.; Wan, X.; Wang, J.; Meng, Q.; Zhang, H.; Jiang, L.; Zhang, Z. Org. Lett. 2005, 7, 5425.(d) Wan, X.; Meng, Q.; Zhang, H.; Sun, Y.; Fan, W.; Zhang, Z. Org. Lett. 2007, 9, 5613.(e) Meng, Q.; Sun, Y.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Zhang, Z. J. Org. Chem. 2008, 73, 3842.(f) Tao, X.; Li, W.; Ma, X.; Li, X.; Fan, W.; Xie, X.; Ayad, T.; Ratovelomanana-Vidal, V.; Zhang, Z. J. Org. Chem. 2011, 77, 612.(g) Xu, H.; Meng, Q.; Zhang, Z. Chin. J. Chem. 2008, 26, 1656.

[8] (a) Herold, P.; Indolese, A. F.; Studer, M.; Jalett, H. P.; Siegrist, U.; Blaser, H. U. Tetrahedron 2000, 56, 6497.(b) Blaser, H. U.; Eissen, M.; Fauquex, P. F.; Hungerbühler, K.; Schmidt, E.; Sedelmier, G.; Studer, M. In Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Eds.: Blaser, H. U., Schmidt, E., Wiley-VCH, Weinheilm, 2004, p. 91.

[9] Meng, Q.; Zhu, L.; Zhang, Z. J. Org. Chem. 2008, 73, 7209.

[10] (a) Zhu, L.; Chen, H.; Meng, Q.; Fan, W.; Xie, X.; Zhang, Z. Tetrahedron 2011, 67, 6186.(b) Zhu, L.; Meng, Q.; Fan, W.; Xie, X.; Zhang, Z. J. Org. Chem. 2010, 75, 6027.

[11] Fan, W.; Li, W.; Ma, X.; Tao, X.; Li, X.; Yao, Y.; Xie, X.; Zhang, Z. J. Org. Chem. 2011, 76, 9444.

[12] (a) Andrushko, N.; Andrushko, V.; Tararov, V.; Korostylev, A.; K?nig, G.; B?rner, A. Chirality 2010, 22, 534.(b) Ager, D. J.; De Vries, A. H. M.; De Vries, J. G. Chem. Soc. Rev. 2012, 41, 3340.

[13] Yao, Y.; Fan, W.; Li, W.; Ma, X.; Zhu, L.; Xie, X.; Zhang, Z. J. Org. Chem. 2011, 76, 2807.

[14] (a) Shao, L.; Seki, T.; Kawano, H.; Saburi, M. Tetrahedron Lett. 1991, 32, 7699.(b) Shao, L.; Kawano, H.; Saburi, M.; Uchida, Y. Tetrahedron 1993, 49, 1997.(c) Blandin, V.; Carpentier, J.-F.; Mortreux, A. Eur. J. Org. Chem. 1999, 3421.(d) Blandin, V.; Carpentier, J.-F.; Mortreux, A. Eur. J. Org. Chem. 1999, 1787.(e) Blandin, V.; Carpentier, J.-F.; Mortreux, A. New J. Chem. 2000, 24, 309.

[15] Fan, W.; Li, W.; Ma, X.; Tao, X.; Li, X.; Yao, Y.; Xie, X.; Zhang, Z. Chem. Commun. 2012, 48, 4247.

[16] (a) Hiersemann, M.; Nubbemeyer, U. The Claisen Rearrangement: Methods and Applications, Wiley-VCH, Weinheim, 2007.(b) Wipf, P. In In Comprehensive Organic Synthesis, Vol. 5, Eds.: Trost, B.; Fleming, I.; Paquette, L., Pergamon, Kidlington, Oxford, 1991, p. 827.

[17] Stork, G.; Schoofs, A. R. J. Am. Chem. Soc. 1979, 101, 5081.

[18] (a) Yamaguchi, S.; Mosher, H. S. J. Org. Chem. 1973, 38, 1870.(b) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.(c) Terashima, S.; Tanno, N.; Koga, K. J. Chem. Soc., Chem. Commun. 1980, 1026.

[19] (a) Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16.(b) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.

[20] (a) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.(b) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529.(c) Arai, N.; Azuma, K.; Nii, N.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 7457.

[21] (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.(b) Reiff, E. A.; Nair, S. K.; Narayan Reddy, B. S.; Inagaki, J.; Henri, J. T.; Greiner, J. F.; Georg, G. I. Tetrahedron Lett. 2004, 45, 5845.

[22] Ma, X.; Li, W.; Li, X.; Tao, X.; Fan, W.; Xie, X.; Ratovelomanana- Vidal, V.; Ayad, T.; Zhang, Z. Chem. Commun. 2012, 48, 5352.

[23] Li, W.; Ma, X.; Fan, W.; Tao, X.; Li, X.; Xie, X.; Zhang, Z. Org. Lett. 2011, 13, 3876.

[24] Li, W.; Fan, W.; Ma, X.; Tao, X.; Li, X. Zhang, Z. In 7th Chinese Chemical Society National Organic Chemistry Conference, Nanjing, 2011, p. 35 (in Chinese).(李万方, 范为正, 马欣, 陶晓明, 李晓明, 张兆国, 第七届全国有机化学学术会议, 南京, 2011, p. 35).

[25] Li, W.; Xie, X.; Tao, X.; Ma, X.; Fan, W.; Li, X.; Zhang, Z. RSC Adv. 2012, 2, 3214.
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