메뉴 건너뛰기




Volumn 120, Issue 26, 1998, Pages 6477-6487

Catalytic asymmetric synthesis of quaternary carbon centers. Exploratory investigations of intramolecular heck reactions of (E)-α,β-unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; SPIRO COMPOUND;

EID: 0032496952     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980786p     Document Type: Article
Times cited : (268)

References (51)
  • 3
    • 33748647785 scopus 로고
    • One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 2379
    • De Meijere, A.1    Meyer, F.E.2
  • 4
    • 0347891354 scopus 로고    scopus 로고
    • Liebeskind, L. S., Ed.; JAI: Greenwich
    • One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
    • (1996) Advances in Metal-Organic Chemistry , pp. 249-252
    • Jeffery, T.1
  • 5
    • 0001656364 scopus 로고    scopus 로고
    • One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
    • (1996) Contemp. Org. Synth. , vol.3 , pp. 447
    • Gibson, S.E.1    Middleton, R.J.2
  • 6
    • 0037782994 scopus 로고    scopus 로고
    • Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Chapter 3
    • One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
    • (1998) Metal-catalyzed Cross-coupling Reactions
    • Bräse, S.1    De Meijere, A.2
  • 9
    • 0002654419 scopus 로고    scopus 로고
    • Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Chapter 6
    • The application of intramolecular Heck reactions in natural products synthesis has been recently reviewed: Link, J. T.; Overman, L. E. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 6.
    • (1998) Metal-catalyzed Cross-coupling Reactions
    • Link, J.T.1    Overman, L.E.2
  • 10
    • 0003431335 scopus 로고    scopus 로고
    • Liebeskind, L. S., Ed.; JAI: Greenwich
    • For recent reviews, see: (a) Shibasaki, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 119-151. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
    • (1996) Advances in Metal-Organic Chemistry , pp. 119-151
    • Shibasaki, M.1
  • 11
    • 0030995738 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Shibasaki, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 119-151. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
    • (1997) Tetrahedron , vol.53 , pp. 7371
    • Shibasaki, M.1    Boden, C.D.J.2    Kojima, A.3
  • 17
    • 0005515344 scopus 로고
    • Early parts of these investigations were described in a preliminary communication: Ashimori, A.; Overman, L. E. J. Org. Chem. 1992, 57, 4571.
    • (1992) J. Org. Chem. , vol.57 , pp. 4571
    • Ashimori, A.1    Overman, L.E.2
  • 28
    • 2642640908 scopus 로고
    • Lebedinskiî, V. V.; Simanovskiî, P. V.; Slutsker, O. D. Izvest. Sektora Platiny i Drugikh Blagorodnykh Metal., Inst. Obshcheî Neorg. Khim., Akad. Nauk S.S.S.R. 1948, 43. Chem. Abstr. 1950, 44, 9293.
    • (1950) Chem. Abstr. , vol.44 , pp. 9293
  • 34
    • 84909809091 scopus 로고
    • (a) Absolute configuration was assigned by the method of Rogers: Rogers, D. Acta Crystallogr. 1981, A37, 734.
    • (1981) Acta Crystallogr. , vol.A37 , pp. 734
    • Rogers, D.1
  • 35
    • 2642676495 scopus 로고    scopus 로고
    • note
    • (b) The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 48
    • 2642642561 scopus 로고    scopus 로고
    • note
    • Barton deoxygenation of the xanthate derivative and Wolf-Kishner reduction of the tosylhydrazone derivative failed. Attempts to prepare the tosylate or iodide derivative of the corresponding primary alcohol, as a prelude to reduction, were also unsuccessful.
  • 50
    • 0028556311 scopus 로고
    • 3 and BINAP were purchased from Aldrich Chemical Co. High-resolution mass spectra were measured on a MicroMass Analytical 7070E spectrometer (EI or CI-isobutane); uncertainty (s) in mass measurements is 1.0 millimass unit (molecular weight < 400) or 1.5 millimass units (molecular weight 400-1000). Other general experimental details have been described: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11241
    • Deng, W.1    Overman, L.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.