Palladium-catalyzed synthesis of stereodefined 3-[(1,1-unsymmetrically disubstituted)methylidene]isobenzofuran-1(3H)-ones and stereodefined 5-[(1,1- unsymmetrically disubstituted)methylidene]furan-2(5H)-ones

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5281-5286

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

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF MOLISE   (Italy)

Author keywords

Alkynes; Furanones; Isobenzofuranones; Palladium and reactions

Indexed keywords

ALKYNE; BENZOIC ACID DERIVATIVE; FURANONE DERIVATIVE; HALIDE; PALLADIUM; POTASSIUM SALT;

ARTICLE; CATALYSIS; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

EID: 0034234561     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00806-6     Document Type: Article

References (27)

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3. (c) Kotora, M.; Negishi, E. Synthesis 1997, 121-128;
4. (d) Kotora, M.; Negishi, E. Tetrahedron 1997, 53, 6707-6738, and references cited therein;
5. (e) Kundu, N. G.; Pal, M.; Nandi, B. J. Chem. Soc., Perkin Trans. 1 1998, 561-568;
6. (f) Sashida, H.; Kawamukai, A. Synthesis 1999, 1145-1148.
7. (a) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135-156;
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13. For the synthesis of 3,4-disubstituted isocoumarins, see: (a) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. J. Org. Chem. 1995, 60, 3270-3271;
14. (b) Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770-8779.
15. 3): δ 162.79 (C-1), 154.97 (C-3), 138.83 (C-5), 134.49 (C-7), 134.38 (C-1′), 130.66 (C-2′), 130.66 (C-6′), 129.42 (C-9), 128.91 (C-3′), 128.91 (C-5′), 128.08 (C-4′), 127.38 (C-8), 124.75 (C-6), 120.05 (C-10), 116.39 (C-4), 33.23 (C-11), 20.97 (C-12), 13.63 ppm (C-13).
16. Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387-6389.
17. (a) Arcadi, A.; Burini, A.; Cacchi, S.; Del Mastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976-982;
18. (b) Boussy, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1992, 33, 2811-2814;
19. (c) Boussy, D.; Gore, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett. 1993, 34, 3129-3130;
20. (d) Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254-2255;
21. (e) Wu, M.-J.; Wei, L.-M.; Lin, C.-F. 10th Symposium on Organometallic Chemistry directed towards Organic Synthesis; Versailles, France, 18-22 July 1999, Abstracts P-521.
22. 4 and 4 mol% CuI, followed by saponification of the so obtained methyl (Z)-2-en-4-ynoates with 1 M LiOH at 20°C and acidification of the resulting lithium carboxylates.
23. 3): δ 164.83 (C-6), 162.26 (C-2), 150.20 (C-15), 149.99 (C-11), 146.23 (C-4), 137.36 (C-13), 132.93 (C-14), 123.03 (C-12), 117.07 (C-5), 113.13 (C-3), 31.39 (C-7), 29.61 (C-8), 22.36 (C-9), 18.20 (C-16), 13.65 ppm (C-10).
24. For similar values of this coupling constant in 5-substituted and/or 5,6-disubstituted 2H-pyran-2-ones, see: (a) Pirkle, W. H.; Dines, M. J. Heterocyclic Chem. 1969, 6, 1-3;
25. (b) Schlingmann, G.; Milne, L.; Carter, G. T. Tetrahedron 1998, 54, 13013-13022.
26. For similar values of this coupling constant in 5-ylidene-2(5H)-furanones, see: (a) Ref. 1e;
27. (b) Rousset, M.; Abarbri, M.; Thibounet, J.; Duchêne, A.; Parrain, J.-L. Org. Lett. 1999, 1, 701-703.