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Noyori Catalytic Asymmetric Hydrogenation

Noyori Catalytic Asymmetric Hydrogenation. Wang jiahao Jiahao.w@sjtu.edu.cn. Description. Pharmaceuticals Agrochemicals Flavors Other fine chemicals. President, RIKEN & University Professor, Nagoya University

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Noyori Catalytic Asymmetric Hydrogenation

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  1. Noyori Catalytic Asymmetric Hydrogenation Wang jiahao Jiahao.w@sjtu.edu.cn

  2. Description • Pharmaceuticals • Agrochemicals • Flavors • Other fine chemicals

  3. President, RIKEN & University Professor, Nagoya University Birth:Kobe, Japan; 1938.Education:Bachelor: Kyoto University (Professor K. Sisido), 1961.Master: Kyoto University (Professor K. Sisido), 1963.Ph.D.: Kyoto University (Professor H. Nozaki), 1967.Postdoctoral Fellow: Harvard University (Professor E. J. Corey), 1969–1970. Publications: Over 500 (original papers, reviews, chapters, commentaries, and monographs).ISI citations, ca. 35,000; h-index, 101. Patents:Over 250.

  4. Historical Perspective • Mechanism • Variations and Improvements • Synthetic utility

  5. Historical Perspective Knowles, W. S.; Sabacky, M. J. Chem. Commun. 1968, 1445-1446. Horner, L.; Siegel, H.; BUthe, H. Angew. Chem. Int. Ed. Engl. 1968, 7, 942. Dang, T. P.; Kagan, H. B. J. Chem. Soc. Chem. Commun. 1971, 481. 3-15% ee DIOP 72% ee

  6. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc. Chem. Commun. 1972, 10-11. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L. Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.

  7. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc. Chem. Commun. 1972, 10-11. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L. Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952. S/C=20000:1 Monsanto L-DOPA process.

  8. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc. Chem. Commun. 1972, 10-11. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L. Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.

  9. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc. Chem. Commun. 1972, 10-11. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L. Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.

  10. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934.

  11. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932–7934. Shimizu, Hideo; Nagasaki, Izuru; Matsumura, Kazuhiko; Sayo, Noboru; Saito, Takao. Acc. Chem. Res. 2007, 40, 1385–1393. Synthesis of BINAP 1980

  12. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629–635. Shimizu, Hideo; Nagasaki, Izuru; Matsumura, Kazuhiko; Sayo, Noboru; Saito, Takao. Acc. Chem. Res. 2007, 40, 1385–1393. Synthesis of BINAP 1986

  13. Sayo, N.; Zhang, X.; Ohmoto, T.; Yoshida, A.; Yokozawa, T. Eur. Patent 0,771,812, 1997. Shimizu, Hideo; Nagasaki, Izuru; Matsumura, Kazuhiko; Sayo, Noboru; Saito, Takao. Acc. Chem. Res. 2007, 40, 1385–1393. Synthesis of BINAP 1997

  14. Mechanism Burk, M. J. Acc. Chem. Res. 2000, 33, 363-372. van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; deVries, A. H. M.; deVries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540. Claver, C.; Fernandez, E.; Gillon, A,; Heslop, K.; Hyett, D. J.; Martorell, A,; Orpen, A. G.; Pringle, P. G. Chem. Commun.2000, 961-962. Reetz, M. T.; Mehler, G. Angew. Chem. Int. Ed. 2000, 39, 3889-3890. Gridnev, 1. D.; Higashi, N.; Asakura, K.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 7183-7194. DuPhos Unsaturated dihydride mechanism

  15. Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem. 1988, 27, 566-569. Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org, Chem. 1992, 57, 4053-4054. Functionalized olefins including enamides, α, β- and α, γ-unsaturated carboxylic acids, allylic and homoallylic alcohols，as well as various functionalized ketones.

  16. Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org, Chem. 1992, 57, 4053-4054.

  17. Kitamura, Masato; Nakatsuka, Hiroshi. Chem. Commun. 2011, 842-846. Unsaturated monohydride mechanism

  18. Wiles, J. A.; Bergens, S. H.; Young, Y. G. J. Am. Chem. Soc. 1997, 119, 2940-2941. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858. Mashima. K.; Kusano, K.; Ohta, T.; Noyori, R.; Takaya, H. J. Chem. Soc. Chem. Commun. 1989, 1208-1210.

  19. Variations and Improvements

  20. Tang, W.; Chi, Y.; Zhang, X. Org. Lett. 2002, 4, 1695-1698.

  21. Tang, W.; Chi, Y.; Zhang, X. Org. Lett. 2002, 4, 1695-1698. Suzuki coupling Ullmann coupling (+)-DTTA=(+)-(2R,3R)-2,3-o-ditoluoyltartric acid

  22. Tang, W.; Chi, Y.; Zhang, X. Org. Lett. 2002, 4, 1695-1698. S/C=100:1 S/C=2000:1

  23. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264–267. Shimizu, Hideo; Nagasaki, Izuru; Matsumura, Kazuhiko; Sayo, Noboru; Saito, Takao. Acc. Chem. Res. 2007, 40, 1385–1393.

  24. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264–267. Shimizu, Hideo; Nagasaki, Izuru; Matsumura, Kazuhiko; Sayo, Noboru; Saito, Takao. Acc. Chem. Res. 2007, 40, 1385–1393.

  25. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264–267. Shimizu, Hideo; Nagasaki, Izuru; Matsumura, Kazuhiko; Sayo, Noboru; Saito, Takao. Acc. Chem. Res. 2007, 40, 1385–1393.

  26. Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron2005, 61, 5405–5432. Shimizu, Hideo; Nagasaki, Izuru; Matsumura, Kazuhiko; Sayo, Noboru; Saito, Takao. Acc. Chem. Res. 2007, 40, 1385–1393. SEGPHOS Series DTBM-SEGPHOS

  27. Synthetic Utility 1. Hydrogenation of dehydroamino acid derivatives Sub= (Z)- or (E)-α-(acylamino)acrylic acids or esters DuPhos Burk, M. J.; Feaster, J. E.; Nugent, W. A,; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.

  28. Burk, M. J.; Feaster, J. E.; Nugent, W. A,; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.

  29. Sub= β, β - disubstituted α-dehydroamino acids or esters (S,S)-Me-BPE Burk, M. J.; Bedingfield. K. M.; Kiesman, W. F.; Allen, J. G. Tetrahedron Lett. 1999, 40, 3093-3096.

  30. Burk, M. J.; Bedingfield. K. M.; Kiesman, W. F.; Allen, J. G. Tetrahedron Lett. 1999, 40, 3093-3096.

  31. 2. Hydrogenation of enamides 99.5% ee 99% ee

  32. 3. Hydrogenation of ( β-acylamino) acrylates BINAP, DuPhos, BICP, BDPMI and MalPHOS catalyst: (S)-XylyI-o-BINAPO-Ru, (99% ee) catalyst: (S,S,R,R)-TangPhos-Rh, (93.8% ee) TangPhos Up to 99.6% ee Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159-4161.

  33. Ru-Me-DuPhos, 87.8% ee Rh-BICP, 86.9% ee Ru-BINAP, 5% ee TON=200 Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159-4161.

  34. 4. Hydrogenation of enol esters Wu, S.; Wang, W.; Tang, W.; Lin, M.; Zhang, X.; Org. Lett. 2002, 4, 4495-4497.

  35. TON=100 Wu, S.; Wang, W.; Tang, W.; Lin, M.; Zhang, X.; Org. Lett. 2002, 4, 4495-4497.

  36. 5. Hydrogenation of α-β unsaturated carbonyls

  37. 6. Hydrogenation of unsaturated alcohols

  38. 谢 谢！

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