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Volumn 9, Issue 12, 2003, Pages 2797-2811

Synthesis of enantiomerically enriched propargylamines by copper-catalyzed addition of alkynes to enamines

Author keywords

Alkynes; Amines; Asymmetric catalysis; C H activation; Copper catalysis

Indexed keywords

ADDITION REACTIONS; CATALYSIS; COPPER; SALTS; SYNTHESIS (CHEMICAL);

EID: 0037775564     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204691     Document Type: Article
Times cited : (129)

References (47)
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    • For a very efficient Zn-catalyzed enantioselective addition of alkynes to aldehydes, see: a) N. K. Anand, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 9687; b) E. El-Sayed, N. K. Anand, E. M. Carreira, Org. Lett. 2001, 3, 3017; c) D. E. Frantz, R. Faessler, C. S. Tomooka, E. M. Carreira, Acc. Chem. Res. 2000, 33, 373; d) D. E. Frantz, R. Faessler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806.
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    • For a very efficient Zn-catalyzed enantioselective addition of alkynes to aldehydes, see: a) N. K. Anand, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 9687; b) E. El-Sayed, N. K. Anand, E. M. Carreira, Org. Lett. 2001, 3, 3017; c) D. E. Frantz, R. Faessler, C. S. Tomooka, E. M. Carreira, Acc. Chem. Res. 2000, 33, 373; d) D. E. Frantz, R. Faessler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806.
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    • For a copper chloride-catalyzed reaction of alkynes with enamines, see: a) K. C. Brannock, R. D. Burpitt, J. G. Thweatt, J. Org. Chem. 1963, 28, 1462; see also: b) J. J. McNally, M. A. Youngman, S. L. Dax, Tetrahedron Lett. 1998, 39, 967; c) M. A. Youngman, S. L. Dax, Tetrahedron Lett. 1997, 38, 6347.
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    • note
    • This enamine (95% yield) was prepared according to ref. [13] with TsCI (1 equiv).
  • 35
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    • note
    • 2 by fullmatrix least-squares methods (SHELXS-86, SHELXL-93). All nonhydrogen atoms were refined anisotropically. R1 = 0.0343, ωR2 = 0.0767 for all data with I > 2σ. CCDC 199761 contains the supplementary crystallographic data (excluding structure factors) and can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.uk).
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    • note
    • The stereochemistry of 11 was established by analysis of NOE data.
  • 42
    • 85007629812 scopus 로고    scopus 로고
    • note
    • 2 by fullmatrix least-squares methods (SHELXS-86, SHELXL-93). All nonhydrogen atoms were refined anisotropically, R1 = 0.0374, ωR2 = 0.0834 for all data with I > 2σ. CCDC 182716 contains the supplementary crystallographic data (excluding structure factors) and can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.