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Volumn 3, Issue 5, 1997, Pages 726-731

Addition of organozincate reagents to imines derived from (S)-1-phenylethylamine and ethyl (S)-valinate-synthesis of (S)-1-(2-pyridyl)alkylamines

Author keywords

amines; asymmetric synthesis; C C coupling; chiral auxiliaries; imines; zinc

Indexed keywords


EID: 0031028779     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030512     Document Type: Article
Times cited : (57)

References (36)
  • 16
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    • 2Zn: a) H. Nehl, W. Scheidt, J. Organomet. Chem. 1985, 289, 1; b) R. Mynott, B. Gabor, H. Lehmkuhl, 1. Doering, Angew. Chem. Int. Ed. Engl. 1985, 24, 335. We assume that the group exchange is slow and that symmetrical species are not formed at the temperatures we used (-78°C) to prepare the mixed zincates.
    • (1985) J. Organomet. Chem. , vol.289 , pp. 1
    • Nehl, H.1    Scheidt, W.2
  • 17
    • 84985502028 scopus 로고
    • 2Zn: a) H. Nehl, W. Scheidt, J. Organomet. Chem. 1985, 289, 1; b) R. Mynott, B. Gabor, H. Lehmkuhl, 1. Doering, Angew. Chem. Int. Ed. Engl. 1985, 24, 335. We assume that the group exchange is slow and that symmetrical species are not formed at the temperatures we used (-78°C) to prepare the mixed zincates.
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 335
    • Mynott, R.1    Gabor, B.2    Lehmkuhl, H.3    Doering, I.4
  • 18
    • 0007139912 scopus 로고
    • For the selectivity of group transfer from mixed zincates to α,β-enones, see ref. [4c-g]. The analogous selectivity of mixed dialkylcuprates is generally not high: a) W. H. Mandeville, G. M. Whitesides, J. Org. Chem. 1974, 39, 400; b) D. E. Bergbreiter, J. M. Killough, ibid. 1976, 41, 2750; c) F. Leyendecker, J. Drouin, J. J. Debesse, J. M. Conia, Tetrahedron Lett. 1977, 1591; d) H. Westmijze, H. Kleijn, P. Vermeer, Synthesis 1978, 454.
    • (1974) J. Org. Chem. , vol.39 , pp. 400
    • Mandeville, W.H.1    Whitesides, G.M.2
  • 19
    • 0000701105 scopus 로고
    • For the selectivity of group transfer from mixed zincates to α,β-enones, see ref. [4c-g]. The analogous selectivity of mixed dialkylcuprates is generally not high: a) W. H. Mandeville, G. M. Whitesides, J. Org. Chem. 1974, 39, 400; b) D. E. Bergbreiter, J. M. Killough, ibid. 1976, 41, 2750; c) F. Leyendecker, J. Drouin, J. J. Debesse, J. M. Conia, Tetrahedron Lett. 1977, 1591; d) H. Westmijze, H. Kleijn, P. Vermeer, Synthesis 1978, 454.
    • (1976) J. Org. Chem. , vol.41 , pp. 2750
    • Bergbreiter, D.E.1    Killough, J.M.2
  • 20
    • 0343366458 scopus 로고
    • For the selectivity of group transfer from mixed zincates to α,β-enones, see ref. [4c-g]. The analogous selectivity of mixed dialkylcuprates is generally not high: a) W. H. Mandeville, G. M. Whitesides, J. Org. Chem. 1974, 39, 400; b) D. E. Bergbreiter, J. M. Killough, ibid. 1976, 41, 2750; c) F. Leyendecker, J. Drouin, J. J. Debesse, J. M. Conia, Tetrahedron Lett. 1977, 1591; d) H. Westmijze, H. Kleijn, P. Vermeer, Synthesis 1978, 454.
    • (1977) Tetrahedron Lett. , pp. 1591
    • Leyendecker, F.1    Drouin, J.2    Debesse, J.J.3    Conia, J.M.4
  • 21
    • 84981682355 scopus 로고
    • For the selectivity of group transfer from mixed zincates to α,β-enones, see ref. [4c-g]. The analogous selectivity of mixed dialkylcuprates is generally not high: a) W. H. Mandeville, G. M. Whitesides, J. Org. Chem. 1974, 39, 400; b) D. E. Bergbreiter, J. M. Killough, ibid. 1976, 41, 2750; c) F. Leyendecker, J. Drouin, J. J. Debesse, J. M. Conia, Tetrahedron Lett. 1977, 1591; d) H. Westmijze, H. Kleijn, P. Vermeer, Synthesis 1978, 454.
    • (1978) Synthesis , pp. 454
    • Westmijze, H.1    Kleijn, H.2    Vermeer, P.3
  • 27
    • 33845280557 scopus 로고
    • 3 has been demonstrated: a) B. H. Lipshutz, E. L. Ellsworth, T. J. Siahaan, J. Am. Chem. Soc. 1988, 110, 4834; b) B. H. Lipshutz, E. L. Ellsworth, T. J. Siahaan, J. Am. Chem. Soc. 1989, 111, 1351; c) B. H. Lipshutz, E. L. Ellsworth, S. H. Dimock, ibid. 1988, 110, 4834.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4834
    • Lipshutz, B.H.1    Ellsworth, E.L.2    Siahaan, T.J.3
  • 28
    • 0038753596 scopus 로고
    • 3 has been demonstrated: a) B. H. Lipshutz, E. L. Ellsworth, T. J. Siahaan, J. Am. Chem. Soc. 1988, 110, 4834; b) B. H. Lipshutz, E. L. Ellsworth, T. J. Siahaan, J. Am. Chem. Soc. 1989, 111, 1351; c) B. H. Lipshutz, E. L. Ellsworth, S. H. Dimock, ibid. 1988, 110, 4834.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1351
    • Lipshutz, B.H.1    Ellsworth, E.L.2    Siahaan, T.J.3
  • 29
    • 33845280557 scopus 로고
    • 3 has been demonstrated: a) B. H. Lipshutz, E. L. Ellsworth, T. J. Siahaan, J. Am. Chem. Soc. 1988, 110, 4834; b) B. H. Lipshutz, E. L. Ellsworth, T. J. Siahaan, J. Am. Chem. Soc. 1989, 111, 1351; c) B. H. Lipshutz, E. L. Ellsworth, S. H. Dimock, ibid. 1988, 110, 4834.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4834
    • Lipshutz, B.H.1    Ellsworth, E.L.2    Dimock, S.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.