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Volumn 52, Issue 38, 1996, Pages 12571-12586

Diastereoselective addition of methyllithium and dimethylcuprate-boron trifluoride to imines derived from (S)-1-phenylethylamine

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

EID: 0030590484     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00746-6     Document Type: Article
Times cited : (44)

References (102)
  • 1
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    • 1. (a) Volkmann, R. A. in Comprehensive Organic Synthesis, Trost, B. M. Ed.; Pergamon Press, New York. 1991; Vol. 1, pp. 356-.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 356
    • Volkmann, R.A.1
  • 2
    • 0002874867 scopus 로고
    • Patai, S. Ed., Interscience, New York
    • (b) Harada, K. in "The Chemistry of Carbon-Nitrogen Bond", Patai, S. Ed., Interscience, New York. 1970; Vol. 6, p. 266.
    • (1970) The Chemistry of Carbon-nitrogen Bond , vol.6 , pp. 266
    • Harada, K.1
  • 6
    • 0000389840 scopus 로고
    • The addition of methylmagnesium iodide to the imines derived from (S)- and (R)-1-phenylethanamine and (-)-menthyl glyoxylate (double asymmetric induction, principally dictated by the menthyl group) was reported
    • (c) Hallet, D. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1995, 657. The addition of methylmagnesium iodide to the imines derived from (S)- and (R)-1-phenylethanamine and (-)-menthyl glyoxylate (double asymmetric induction, principally dictated by the menthyl group) was reported:
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 657
    • Hallet, D.J.1    Thomas, E.J.2
  • 21
    • 0000752271 scopus 로고
    • In this preliminary communication the configuration of the amine 4h was erroneously assigned
    • 8. Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron: Asymmetry 1990, 1, 291. In this preliminary communication the configuration of the amine 4h was erroneously assigned.
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 291
    • Boga, C.S.1    Avoia, D.2    Umani-Ronchi, A.3
  • 22
    • 85030274374 scopus 로고    scopus 로고
    • note
    • 3), 136 (67), 91 (23), 119 (20), 255 (17), 120 (12), 77 (10), 105 (10), 269 (3, M+). The mass spectra of all the observed 1,2-diamines 9 had generally the most abundant ions at m/z = (M/2)+. Two unidentified isomeric compounds produced in low yield from 1i had m/z 105 (100), 72 (56), 216 (53), 112 (50), 176 (34), 79 (20), 106 (15), 55 (14), 77 (12).
  • 23
    • 0011886447 scopus 로고
    • 3Li is apparently analogous to the coloured charge transfer complexes of lithium (a) and zinc (b) reagents with mono- and bidentate heteroaromatic ligands: (a) Watson, S. C.; Eastham, J. F. J. Organometal. Chem. 1967, 9, 168.
    • (1967) J. Organometal. Chem. , vol.9 , pp. 168
    • Watson, S.C.1    Eastham, J.F.2
  • 25
    • 84982065503 scopus 로고
    • 11. (a) Kaim., W. Chem. Ber. 1981, 114, 3789.
    • (1981) Chem. Ber. , vol.114 , pp. 3789
    • Kaim, W.1
  • 37
    • 0002446724 scopus 로고
    • Trost, B. M. Ed., Pergamon Press, London and New York
    • 4b to imines: (a) Roush, W. R. in Comprehensive Organic Synthesis, Trost, B. M. Ed., Pergamon Press, London and New York, 1991, Vol. 2, p. 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1
    • Roush, W.R.1
  • 39
    • 0001705805 scopus 로고
    • E/Z isomerization of an iminium ion
    • (c) Ojima, I.; Inaba, S.-i. Tetarahedron Lett. 1980, 21, 2081. E/Z isomerization of an iminium ion:
    • (1980) Tetarahedron Lett. , vol.21 , pp. 2081
    • Ojima, I.1    Inaba, S.-I.2
  • 41
    • 0030200995 scopus 로고    scopus 로고
    • 18. The same approach was used by us to explain the opposite diastereoselectivity exhibited by allyltin trihalides with respect to allylzinc bromide and allyllead bromide in the addition to methyl (S)-N-(2-pyridinemethylidene) valinate: Alvaro, G; Savoia, D.; Tetrahedron: Asymmetry 1996, 7, 2083.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2083
    • Alvaro, G.1    Savoia, D.2
  • 45
    • 9844239897 scopus 로고
    • 20. In THF solutions of butyllithium an equilibrium is established between the tetramer and the more reactive dimer: (a) McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1805
    • McGarrity, J.F.1    Ogle, C.A.2
  • 89
    • 0029123450 scopus 로고
    • A ß- or γ-heterosubstituent stabilizes organolithium compounds by intramolecular chelation
    • (d) Kauffmann, T. Synthesis 1995, 745. A ß- or γ-heterosubstituent stabilizes organolithium compounds by intramolecular chelation:
    • (1995) Synthesis , pp. 745
    • Kauffmann, T.1
  • 91
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    • 2Mg forms a more stable chelate with 4-methoxy-2-butanone than with methoxyacetone
    • 2Mg forms a more stable chelate with 4-methoxy-2-butanone than with methoxyacetone:
    • (1986) Acc. Chem. Res. , vol.79 , pp. 356
    • Beak, P.1    Meyers, A.I.2
  • 97
    • 33748217152 scopus 로고    scopus 로고
    • 30. The alkylation of N-benzylideneaniline by lithium trimethylferrate has been assumed to proceed through the attack of the nucleophilic iron to the C=N bond, followed by a reductive elimination step, and/or a SET process: Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 386.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 386
    • Kauffmann, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.