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Volumn 37, Issue 22, 1998, Pages 3186-3188

Catalytic, enantioselective synthesis of α-aminonitriles with a novel zirconium catalyst

Author keywords

Amino acids; Asymmetric catalysis; Asymmetric synthesis; Lewis acids; Zirconium

Indexed keywords

AMINO ACID; NITRILE; ZIRCONIUM;

EID: 0032484050     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981204)37:22<3186::AID-ANIE3186>3.0.CO;2-E     Document Type: Article
Times cited : (175)

References (35)
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    • Reviews, a) R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; b) R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889-917; c) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; see also: d) H. Kunz, K. Rück, Angew. Chem. 1993, 705, 355-377; Angew. Chem. Int. Ed. Engl. 1993, 32, 336-358, and references therein; e) F. A. Davis, R. E. Reddy, P. S. Portonovo, Tetrahedron Lett. 1994, 35, 9351-9354; f) T. K. Chakraborty, K. A. Hussain, G. V. Reddy, Tetrahedron 1995, 51, 9179-9190.
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    • Reviews, a) R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; b) R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889-917; c) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; see also: d) H. Kunz, K. Rück, Angew. Chem. 1993, 705, 355-377; Angew. Chem. Int. Ed. Engl. 1993, 32, 336-358, and references therein; e) F. A. Davis, R. E. Reddy, P. S. Portonovo, Tetrahedron Lett. 1994, 35, 9351-9354; f) T. K. Chakraborty, K. A. Hussain, G. V. Reddy, Tetrahedron 1995, 51, 9179-9190.
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    • Quite recently, Jacobsen et al. reported elegant catalytic asymmetric Strecker reactions: a) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; b) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 5315-5316.
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    • Terada, M.1    Motoyama, Y.2    Mikami, K.3
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    • 3SnCN is commercially available: a) J. G. A. Luijten, G. J. M. van der Kerk, Investigations in the Field of Organotin Chemistry, Tin Research Institute, Greenford, 1995, p. 106; b) M. Tanaka, Tetrahedron Lett. 1980, 21, 2959-2962; c) S. Harusawa, R. Yoneda, Y. Omori, T. Kurihara, Tetrahedron Lett. 1987, 28, 4189-4190.
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    • 3SnCN is commercially available: a) J. G. A. Luijten, G. J. M. van der Kerk, Investigations in the Field of Organotin Chemistry, Tin Research Institute, Greenford, 1995, p. 106; b) M. Tanaka, Tetrahedron Lett. 1980, 21, 2959-2962; c) S. Harusawa, R. Yoneda, Y. Omori, T. Kurihara, Tetrahedron Lett. 1987, 28, 4189-4190.
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    • 3SnCN is commercially available: a) J. G. A. Luijten, G. J. M. van der Kerk, Investigations in the Field of Organotin Chemistry, Tin Research Institute, Greenford, 1995, p. 106; b) M. Tanaka, Tetrahedron Lett. 1980, 21, 2959-2962; c) S. Harusawa, R. Yoneda, Y. Omori, T. Kurihara, Tetrahedron Lett. 1987, 28, 4189-4190.
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    • note
    • 4, 1 equiv of (R)-6-Br-BINOL, 1 equiv of (R)-3-Br-BINOL). and 3 equiv of NMI.
  • 29
    • 0344205301 scopus 로고    scopus 로고
    • note
    • When TMSCN was used in this system, moderate yields and moderate enantiomeric excesses were observed. The reaction of the aldimine prepared from 1-naphthaldehyde and 2-aminophenol with TMSCN led to the corresponding a-aminonitrile in 33% yield and with 63% ee; with triethylsilyl cyanide this product was obtained in 65% yield and with 63% ee (not optimized).
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    • 3SnCN (achiral methods). In these reactions, the tin compounds were completely recovered by environmentally friendly chemical processes: S. Kobayashi, T. Busujima. S. Nagayama, Chem. Commun. 1998, 981-982.
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    • note
    • 2O) (Beilstein 4 (3), 1414). (S)-Leucinamide hydrochloride is commercially available (Aldrich).


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