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Volumn 35, Issue 20, 1996, Pages 2374-2376

Enantioselective conjugate addition of dialkyl-zinc reagents to cyclic and acyclic enones catalyzed by chiral copper complexes of new phosphorus amidites

Author keywords

Asymmetric syntheses; Carbon carbon coupling; Copper compounds; Phosphorus compounds; Zinc compounds

Indexed keywords


EID: 0030477791     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199623741     Document Type: Article
Times cited : (326)

References (30)
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    • Other examples: b) G. M. Villacorta, C. P. Rao, S. J. Lippard, J. Am. Chem. Soc. 1988, 110, 3175; c) M. van Klaveren, F. Lambert, D. J. F. M. Eijkelkamp, D. M. Grove, G. van Koten, Tetrahedron Lett. 1994, 35, 6135; d) M. Spescha, G. Rihs Helv. Chim. Acta 1993, 76, 1219.
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    • Villacorta, G.M.1    Rao, C.P.2    Lippard, S.J.3
  • 10
    • 84987539004 scopus 로고
    • Other examples: b) G. M. Villacorta, C. P. Rao, S. J. Lippard, J. Am. Chem. Soc. 1988, 110, 3175; c) M. van Klaveren, F. Lambert, D. J. F. M. Eijkelkamp, D. M. Grove, G. van Koten, Tetrahedron Lett. 1994, 35, 6135; d) M. Spescha, G. Rihs Helv. Chim. Acta 1993, 76, 1219.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 1219
    • Spescha, M.1    Rihs, G.2
  • 14
    • 0029044287 scopus 로고
    • Recently enantioselective 1,4-addition of Grignard reagents to cyclic enones, catalyzed by a Cul complex containing a chiral, bidentate phoshane ligand, has been reported: M. Kanai, K. Tomioka, Tetrahedron Lett. 1995, 36, 4275.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4275
    • Kanai, M.1    Tomioka, K.2
  • 17
    • 0001091776 scopus 로고
    • For a discussion about ligand accelerated asymmetric catalysis, see D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
    • (1995) Angew. Chem. , vol.107 , pp. 1159
    • Berrisford, D.J.1    Bolm, C.2    Sharpless, K.B.3
  • 18
    • 33748983103 scopus 로고
    • For a discussion about ligand accelerated asymmetric catalysis, see D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1059
  • 19
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    • note
    • 2Zn to 3a (4a: yield 76%, ee 32%).
  • 20
    • 85033016770 scopus 로고    scopus 로고
    • note
    • 3; Z = 4. The structure was solved by direct methods and refined to R(F) = 0.120, Rw(F) = 0.131. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-114. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ UK (fax: int. code +(1223)336-033; e-mail: teched@chemcrys.cam.ac.uk).
  • 22
    • 0026518693 scopus 로고
    • All new ligands were remarkably stable to air and fully characterized. The corresponding 3,3′-substituted 2,2′-binaphthols were synthesized according to P. J. Cox, W. Wang, V. Snieckus, Tetrahedron Lett. 1992, 33, 2253.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2253
    • Cox, P.J.1    Wang, W.2    Snieckus, V.3
  • 25
    • 33748726159 scopus 로고
    • D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864; Angew. Chem. Int. Ed. Engl. 1995, 34, 798.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 798
  • 28
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    • Transmetalation of organozinc compounds into the corresponding organocopper reagents is well established: P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117.
    • (1993) Chem. Rev. , vol.93 , pp. 2117
    • Knochel, P.1    Singer, R.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.