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Volumn 110, Issue 2, 1988, Pages 629-631

Homogeneous Asymmetric Hydrogenation of Functionalized Ketones

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EID: 33845278216     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00210a070     Document Type: Article
Times cited : (535)

References (11)
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    • Reviews Morrison, J. D., Ed.; Academic Press: New York Chapter 1. Halpern, J. In Asymmetric Synthesis; Vol. 5, Chapter 2. Koenig, K. E. In Asymmetric Synthesis; Vol. 5, Chapter 3. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff Publishers: Dordrecht, 1986. Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190.
    • Reviews: Kagan, H. B. In Asymmetric Synthesis: Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 1. Halpern, J. In Asymmetric Synthesis; Vol. 5, Chapter 2. Koenig, K. E. In Asymmetric Synthesis; Vol. 5, Chapter 3. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff Publishers: Dordrecht, 1986. Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190.
    • (1985) Asymmetric Synthesis , pp. 5
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  • 2
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    • BINAP = 2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
    • BINAP = 2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl. See: Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7932
    • Miyashita, A.1    Yasuda, A.2    Takaya, H.3    Toriumi, K.4    Ito, T.5    Souchi, T.6    Noyori, R.7
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    • Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174. Kitamura, M,; Hsiao, Yi.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4829. Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem., in press.
    • Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174. Kitamura, M,; Hsiao, Yi.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4829. Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem., in press.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7117
    • Noyori, R.1    Ohta, M.2    Hsiao, Y.3    Kitamura, M.4    Ohta, T.5    Takaya, H.6
  • 5
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    • Reactions with Rh complexes
    • Solodar Ojima, I.; Kogure, T.; Terasaki, T.; Achiwa, K. J. Org. Chem. 1978, 43, 3444. Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Törös, S.; Kollar, L.; Heil, B.; Markò, L. J. Organomet. Chem. 1982, 232, Cl7. Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. Takahashi, H.; Morimoto, T.; Achiwa, K. Chem. Lett. 1987, 855. For homogeneous hydrogenation using chiral Co complexes, see: Ohgo, Y.; Natori, Y.; Takeuchi, S.; Yoshimura, J. Chem. Lett. 1974, 1327.
    • Reactions with Rh complexes: Solodar, J. Chem. Tech. 1975, 421. Ojima, I.; Kogure, T.; Terasaki, T.; Achiwa, K. J. Org. Chem. 1978, 43, 3444. Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Törös, S.; Kollar, L.; Heil, B.; Markò, L. J. Organomet. Chem. 1982, 232, Cl7. Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. Takahashi, H.; Morimoto, T.; Achiwa, K. Chem. Lett. 1987, 855. For homogeneous hydrogenation using chiral Co complexes, see: Ohgo, Y.; Natori, Y.; Takeuchi, S.; Yoshimura, J. Chem. Lett. 1974, 1327.
    • (1975) J. Chem. Tech. , vol.421
  • 7
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    • Reviews Oishi, T.; Akita, H. J. Synth. Org. Chem., Jpn. 1983, 41, 1031. Mori, K.; Sugai, T. J. Synth. Org. Chem., Jpn. 1983, 41, 1044. Whitesides, G. M.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1985, 24, 617. Fujisawa, T.; Sato, T.; Ito, T. J. Synth. Org. Chem., Jpn. 1986, 44, 519. Butt, S.; Roberts, S. M. Nat. Prod. Rep. 1986, 489 and references cited therein. See, also: Seebach, D.; Roggo, S.; Zimmermann, J. In Stereochemistry of Organic and Bioorganic Transformations; Bartmann, W., Sharpless, K. B., Eds.; Verlag Chemie: Weinheim, 1987. Brooks, D. W.; Kellogg, R. P.; Cooper, C. S. J. Org. Chem. 1987, 52, 192.
    • Reviews: Sih, C. J.; Chen, C.-S. Angew. Chem., Int. Ed. Engl. 1984, 23, 570. Oishi, T.; Akita, H. J. Synth. Org. Chem., Jpn. 1983, 41, 1031. Mori, K.; Sugai, T. J. Synth. Org. Chem., Jpn. 1983, 41, 1044. Whitesides, G. M.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1985, 24, 617. Fujisawa, T.; Sato, T.; Ito, T. J. Synth. Org. Chem., Jpn. 1986, 44, 519. Butt, S.; Roberts, S. M. Nat. Prod. Rep. 1986, 489 and references cited therein. See, also: Seebach, D.; Roggo, S.; Zimmermann, J. In Stereochemistry of Organic and Bioorganic Transformations; Bartmann, W., Sharpless, K. B., Eds.; Verlag Chemie: Weinheim, 1987. Brooks, D. W.; Kellogg, R. P.; Cooper, C. S. J. Org. Chem. 1987, 52, 192.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 570
    • Sih, C.J.1    Chen, C.-S.2
  • 9
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    • For stereoselective stoichiometric reductions of functionalized ketones
    • Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233. Evans, D. A.; Chapman, K. T. Tetrahedron Lett. 1986, 27, 5939.
    • For stereoselective stoichiometric reductions of functionalized ketones, see: Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338. Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233. Evans, D. A.; Chapman, K. T. Tetrahedron Lett. 1986, 27, 5939.
    • (1984) Acc. Chem. Res. , vol.17 , pp. 338
    • Oishi, T.1    Nakata, T.2


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