메뉴 건너뛰기




Volumn 103, Issue 8, 2003, Pages 2795-2827

Catalytic enantioselective strecker reactions and analogous syntheses

Author keywords

[No Author keywords available]

Indexed keywords

AMINO NITRILES; CATALYTIC ENANTIOSELECTIVE; HYDROCYANATION; STRECKER REACTIONS;

EID: 0041378065     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr020038p     Document Type: Article
Times cited : (629)

References (101)
  • 2
    • 0028355337 scopus 로고
    • For an overview about the stereoselective synthesis of α-amino acids in general, see (a) Duthaler, R. O. Tetrahedron 1994, 50, 1539
    • (1994) Tetrahedron , vol.50 , pp. 1539
    • Duthaler, R.O.1
  • 6
    • 0003448735 scopus 로고
    • note; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, New York
    • For comprehensive reviews about catalytic asymmetric syntheses, see (a) Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, New York, 1995; Vol. E21.
    • (1995) Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis , vol.E21
  • 8
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
    • (b) Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
    • (1999) Comprehensive Asymmetric Catalysis I-III
  • 9
    • 0035793657 scopus 로고    scopus 로고
    • For a previous brief overview highlighting developments in the field of catalytic asymmetric Strecker reaction, see Yet, L. Angew. Chem., Int. Ed. Engl. 2001, 40, 875.
    • (2001) Angew. Chem., Int. Ed. Engl. , vol.40 , pp. 875
    • Yet, L.1
  • 10
    • 0000862669 scopus 로고    scopus 로고
    • For a general review about nucleophilic addition to imines, see Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    • (1999) Chem. Rev. , vol.99 , pp. 1069
    • Kobayashi, S.1    Ishitani, H.2
  • 16
  • 21
    • 37049128011 scopus 로고
    • note
    • Previously, some Strecker reactions in the presence of optically active amines bases and acids, e.g., (+)-camphor-10-sulfonic acid were carried out, but did not led to an asymmetric induction; see Ogata, Y.; Kawasaki, A. J. Chem. Soc. B 1971, 325.
    • (1971) J. Chem. Soc. B , pp. 325
    • Ogata, Y.1    Kawasaki, A.2
  • 25
    • 0000140586 scopus 로고    scopus 로고
    • For a review about the asymmetric synthesis of cyanohydrins, see Gregory, R. J. H. Chem. Rev. 1999, 99, 3649.
    • (1999) Chem. Rev. , vol.99 , pp. 3649
    • Gregory, R.J.H.1
  • 27
    • 0343196685 scopus 로고    scopus 로고
    • note
    • This important amino acid L-tert-leucine is produced on tons scale at Degussa AG by means of an enzymatic reductive amination process starting from the corresponding α-keto acid; for this reaction concept, see: Krix, G.; Bommarius, A. S.; Drauz, K.; Kottenhahn, M.; Schwarm, M.; Kula, M.-R. J. Biotechnol. 1997, 53, 29.
    • (1997) J. Biotechnol. , vol.53 , pp. 29
    • Krix, G.1    Bommarius, A.S.2    Drauz, K.3    Kottenhahn, M.4    Schwarm, M.5    Kula, M.-R.6
  • 39
    • 84955394357 scopus 로고    scopus 로고
    • Yamamoto, H., Ed.; Wiley-VCH: Weinheim
    • Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000.
    • (2000) Lewis Acids in Organic Synthesis
  • 46
    • 0000345527 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
    • (b) For a review, see Katsuki, T. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 621f.
    • (1999) Comprehensive Asymmetric Catalysis I-III
    • Katsuki, T.1
  • 57
    • 0041497207 scopus 로고    scopus 로고
    • PCT Int. Pat. Appl. WO9956699
    • Jacobsen, E. N.; Sigman, M. S. PCT Int. Pat. Appl. WO9956699, 1999.
    • (1999)
    • Jacobsen, E.N.1    Sigman, M.S.2
  • 61
    • 0041998169 scopus 로고    scopus 로고
    • note
    • For example, the Corey group and Noyori group used chiral bimetallic complexes as catalysts for the asymmetric CBS borane reduction and diethyl zinc addition, respectively; see ref 29 and Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. 1998, 30, 34. Shibasaki et al. developed highly efficient chiral heterobimetallic complexes which have been proven to be efficient catalysts for numerous C-C, C-S, C-P, C-O, and C-H bond forming reactions; see ref 36. A bifunctional catalyst which is based on gold as a metal component and a phosphine ligand containing an additional amine functionality as a Lewis base was found by Ito, Sawamura, and Hayashi; see Hayashi, T.; Sawamura, M.; Ito, Y. Tetrahedron 1992, 48, 1999. The application of this metal complex in the asymmetric aldol reaction gave excellent stereo-selectivities.
  • 79
    • 0042498942 scopus 로고    scopus 로고
    • personal communication
    • (a) Hoveyda, A. H., personal communication
    • Hoveyda, A.H.1
  • 93
    • 0013083033 scopus 로고    scopus 로고
    • Jacobsen, E., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg
    • For a review about the asymmetric catalytic nitroalkane addition to aldehydes which was developed previously by the Shibasaki group, see Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis; Jacobsen, E., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol 3, p 1075f.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Shibasaki, M.1    Gröger, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.