The use of stabilized carbon nucleophiles in palladium(II)-catalyzed 1,4-oxidation of conjugated dienes

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3603-3606

  Rönn, Magnus ^a   Andersson, Pher G ^a   Bäckvall, Jan E ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; INDAN DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037798563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00674-6     Document Type: Article

References (32)

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25. 1H NMR (400 MHz) δ; 7.98 (2 H, m), 7.74 (1 H, m), 7.61 (2 H, m), 5.91 (1 H, m), 5.79 (1 H, m), 5.62 (1 H, app. dt, J= 9.6, 3.7, 1.1 Hz), 5.11 (1 H, m), 3.66 (1 H, ddd, J= 11.3, 5.0, 1.8 Hz), 3.26 (1 H, m), 2.85 (1 H, d, J=7.0 Hz), 2.83 (1 H, d, J=7.0 Hz), 2.40 (1 H, m), 2.09 (1 H, m).
26. NOE in %. equation presented.
27. 15b with stabilized carbon nucleophiles is known to occur with trans stereochemistry: (a) Kurosawa, H.; Majima, T.; Asada, N. J. Am. Chem. Soc. 1980, 102, 6996.
28. (b) Stille, J. K.; Fox, D. B. J. Am. Chem. Soc. 1970, 92, 1274.
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31. Although this elimination has previously assumed to occur via syn β-elimination, recent studies indicate that an anti elimination of a proton and palladium(0) is a competing pathway: Andersson, P. G.; Schab, S. Organometallics 1995, 14, 1.
32. For nucleophilic attack on (π-allyl)palladium complex in DMSO see: Tsuji, J. Tetrahedron Lett. 1965, 4387.