α-amino acidate-Ru(II) catalysts for asymmetric transfer hydrogenation: First utilization of α-amino acids as an efficient ligand

Chemistry Letters

Volumn , Issue 6, 1998, Pages 491-492

  Ohta, Tetsuo ^a   Nakahara, Shu Ichi ^a   Shigemura, Yasuhiko ^a   Hattori, Kouichi ^a   Furukawa, Isao ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001704256     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.491     Document Type: Article

References (16)

1. "Catalytic Asymmetric Synthesis", Ed by I. Ojima, VCH, New York, 1993; "Asymmetric Synthesis", Ed by D. J. Morrison, Academic Press, Orland, 1985, Vol. 5; G. M. Coppola and H. F. Schuster, "Asymmetric Synthesis. Construction of Chiral Moleculas Using Amino Acids", Wiley, New York, 1987; A. Mori, H. Abe, and S. Inoue, Appl. Organomet. Chem., 9, 189 (1995).
2. "Catalytic Asymmetric Synthesis", Ed by I. Ojima, VCH, New York, 1993; "Asymmetric Synthesis", Ed by D. J. Morrison, Academic Press, Orland, 1985, Vol. 5; G. M. Coppola and H. F. Schuster, "Asymmetric Synthesis. Construction of Chiral Moleculas Using Amino Acids", Wiley, New York, 1987; A. Mori, H. Abe, and S. Inoue, Appl. Organomet. Chem., 9, 189 (1995).
3. "Catalytic Asymmetric Synthesis", Ed by I. Ojima, VCH, New York, 1993; "Asymmetric Synthesis", Ed by D. J. Morrison, Academic Press, Orland, 1985, Vol. 5; G. M. Coppola and H. F. Schuster, "Asymmetric Synthesis. Construction of Chiral Moleculas Using Amino Acids", Wiley, New York, 1987; A. Mori, H. Abe, and S. Inoue, Appl. Organomet. Chem., 9, 189 (1995).
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6. 3)), 3.07 (ddd, 1H, J = 16.5, 11, and 5.5 Hz), 3.91 (dt, 1H, J = 11 and 6.5 Hz), 4.36 (br q, 1H, J = 8Hz), 5.25 (d, 1H, J = 6 Hz), 5.41 (d, 1H, J = 6 Hz), 5.47 (d, 1H, J = 6 Hz), 5.53 (d, 1H, J = 6Hz).
7. Stereochemistry of α-amino acids used was as below; 1a: (S)-proline; 1b: (S)-alanine; 1c: (S)-valine; 1d: (S)-isoleucine; 1e: (S)-tert-leucine; 1f: (R)-phenylglycine; 1g: (S)-phenylalanine; 1h: (S)-N-ethylphenylalanine.
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9. 2O = 1.5, 0.30, 254; 3j: Daicel Chiralcel OD-H, hexane / 2-propanol = 49, 0.50, 254; 3k: Daicel Chiralcel OD-H, hexane / 2-propanol = 249, 0.30, 220
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16. S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, and R. Noyori, J. Am. Chem. Soc., 117, 7562 (1995); J. Takehara, S. Hashiguchi, A. Fujii, S. Inoue, T. Ikariya, and R. Noyori, J. Chem. Soc., Chem. Commun., 1996, 233; A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, and R. Noyori, J. Am. Chem. Soc., 118, 2521 (1996); N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, and R. Noyori, J. Am. Chem. Soc., 118, 4916 (1996); S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya, and R. Noyori, Angew. Chem. Int. Ed. Engl. 36, 288 (1997).