Selective palladium-mediated synthesis of racemic 4,5-disubstituted 5H- furan-2-ones from 3-ynoic acids and organic halides

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7599-7602

  Rossi, Renzo ^a   Bellina, Fabio ^a   Biagetti, Matteo ^a   Mannina, Luisa ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF MOLISE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; HALIDE; PALLADIUM;

ANALYTIC METHOD; ARTICLE; CARBOXYLATION; CATALYSIS; COMPLEX FORMATION; CYCLIZATION; DRUG SYNTHESIS; LIGAND BINDING; NONHUMAN;

EID: 0032497671     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01652-9     Document Type: Article

References (25)

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17. 3, 200 MHz): δ 0.92 (t, 3H, J = 7.0 Hz), 1.20 - 1.70 (br m, 6H), 1.50 (d, 3H, J = 6.7 Hz), 2.47 (t, 2H, J = 6.9 Hz), 4.96 (q, 1H, J = 6.7 Hz), 6.02 ppm (s, 1H).
18. 3, 200 MHz): δ 0.92 (t, 3H, J = 7.0 Hz), 1.20 -1.70 (br m, 6H), 1.50 (d, 3H, J = 6.7 Hz), 2.47 (t, 2H, J = 6.9 Hz), 4.96 (q, 1H, J = 6.7 Hz), 6.02 ppm (s, 1H).
19. 8. For other Pd-catalyzed cyclization processes involving 3-ynoic acids in which it was observed that 3-butynoic acid, 1d, did not give the desired cyclization products, see: (a) Yanagihara, N.; Lambert, C.; Iritani, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 2753-2754;
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22. 10. Jas, G. Synthesis 1991, 965-966.
23. 3, 200 MHz): δ 0.87 (t, 3H, J = 7.0 Hz), 1.30 - 1.55 (m, 4H), 2.39 (t, 2H, J = 6.9 Hz), 1.47 (d, 2H, J = 1.8 Hz), 6.02 ppm (s, 1H).
24. 12. For some examples of Pd-catalyzed cross-coupling reactions between compound 7 and homoallylzinc halides, see: Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5225-5227.
25. 4 and 20 mol % CuI.