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Volumn 4, Issue 21, 2002, Pages 3679-3681

Synthesis of 2H-1-benzopyrans via palladacycles with a metal-bonded stereogenic carbon

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ARTICLE;

EID: 0011825560     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0201456     Document Type: Article
Times cited : (53)

References (48)
  • 6
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    • (e) Dyker, G. Chem. Ber. 1997, 130, 1567-1578.
    • (1997) Chem. Ber. , vol.130 , pp. 1567-1578
    • Dyker, G.1
  • 15
    • 0001069010 scopus 로고    scopus 로고
    • Palladacycles with a metal-bonded stereogenic carbon, other than those containing the norbomane skeleton, are rare. See: (a) Hashmi, A. S. K.; Naumann, F.; Bolte, M. Organometallics 1998, 17, 2385-2387.
    • (1998) Organometallics , vol.17 , pp. 2385-2387
    • Hashmi, A.S.K.1    Naumann, F.2    Bolte, M.3
  • 16
    • 0000941054 scopus 로고
    • (b) Munz, D.; Stephan, C.; Dieck, H. T. J. Organomet. Chem. 1991, 407, 413-420. However, cyclopalladated and cycloplatinated complexes with a metal-bonded stereogenic carbon are known and have been prepared in a nonracemic form.
    • (1991) J. Organomet. Chem. , vol.407 , pp. 413-420
    • Munz, D.1    Stephan, C.2    Dieck, H.T.3
  • 33
    • 0003316397 scopus 로고    scopus 로고
    • Depending on the spectator ligands, alkyne insertions to the known palladacycles are often limited to reactions with dimethyl acetylenedicarboxylate (dmad). See: (a) Mateo, C.; Cardenas, D. J.; Fernandez-Rivas, C.; Echavarren, A. M. Chem. Eur. J. 1996, 2, 1596-1606.
    • (1996) Chem. Eur. J. , vol.2 , pp. 1596-1606
    • Mateo, C.1    Cardenas, D.J.2    Fernandez-Rivas, C.3    Echavarren, A.M.4
  • 36
    • 0033303723 scopus 로고    scopus 로고
    • For general references on alkyne insertions to group 10 metalacycles, see: (d) Campora, J.; Palma, P.; Carmona, E. Coord. Chem. Rev. 1999, 193-195, 207-281.
    • (1999) Coord. Chem. Rev. , vol.193-195 , pp. 207-281
    • Campora, J.1    Palma, P.2    Carmona, E.3
  • 42
    • 0042771031 scopus 로고    scopus 로고
    • note
    • 3) α 24.5 (d, J = 27.7 Hz, 1 P), 26.7 (d, J = 27.3 Hz, 1 P)]. However, attempts to isolate this product failed.
  • 43
    • 0034801556 scopus 로고    scopus 로고
    • Stable arylpalladium(II) enolates have been isolated. See: (a) Hartwig, J. F.; Culkin, D. A. J. Am. Chem. Soc. 2001, 123, 5816-5817. Palladium-catalyzed α-arylation of ketones, esters and amides is known.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5816-5817
    • Hartwig, J.F.1    Culkin, D.A.2
  • 46
    • 0043272329 scopus 로고    scopus 로고
    • note
    • The majority of the known alkyne insertion reactions involve metalacycles bearing monodentate ligands; see refs 3a and 7.
  • 47
    • 0043272328 scopus 로고    scopus 로고
    • note
    • Indicative HMBC correlations for benzopyrans 9a and 13:


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