Mercury(II)-Catalyzed Synthesis of Spiro[4.5]decatrienediones from Allenyl Ketones and Comparison with Silver(I)-, Palladium(II)- and Bronsted Acid-Catalyzed Reactions

Advanced Synthesis and Catalysis

Volumn 342, Issue 1, 2000, Pages 40-51

  Hashmi, A Stephen K ^a   Schwarz, Lothar ^a   Bats, J W ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

Allenes; Homogeneous catalysis; Mercury; Palladium; Silver

Indexed keywords

EID: 0346355839     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3897(200001)342:1<40::aid-prac40>3.0.co;2-v     Document Type: Article

References (37)

1. a) R. P. Gajewski, Tetrahedron Lett. 1976, 4125;
2. b) R. A. Haack, K. R. Beck, Tetrahedron Lett. 1989, 30, 1605;
3. c) F. T. Boyle, Z. S. Masusiak, O. Hares, D. A. Whiting, J. Chem. Soc., Chem. Commun. 1990, 518;
4. d) F. T. Boyle, O. Hares, Z. S. Matusiak, W. Li, D. A. Whiting, J. Chem. Soc., Perkin Trans. 1 1997, 2707
5. J. S. Swenton, A. Callinan, Y. Chen, J. J. Rohde, M. L. Kerns, G. W. Morrow, J. Org. Chem. 1996, 61, 1267
6. For a review see: C. H. Heathcock, S. L. Graham, M. C. Pirrung F. Plavac, C. T. White in The Total Synthesis of Natural Products; J. ApSimon (Ed.); Wiley-Interscience: New York 1983; Vol. 5, pp 264
7. Y. Nagao, W. S. Lee, I.-L. Jeong, M. Shiro, Tetrahedron Lett. 1995, 36, 2799
8. a) J. A. Marshall, E. D. Robinson, J. Org. Chem. 1990, 55, 3450;
9. b) J. A. Marshall, X. Wang, J. Org. Chem. 1991, 56, 960;
10. c) J. A. Marshall, X. Wang, J. Org. Chem. 1992, 57, 3387;
11. d) J. A. Marshall, G. S. Barteley, J. Org. Chem. 1994, 59, 7169;
12. e) J. A. Marshall, E. M. Wallace, P. S. Coan, J. Org. Chem. 1995, 60, 796;
13. f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966;
14. g) J. A. Marshall, J. Liao, J. Org. Chem. 1998, 63, 5962
15. a) A. S. K. Hashmi, Angew. Chem. 1995, 107, 1749; Angew. Chem. Int. Ed. Engl. 1995, 34, 1581;
16. a) A. S. K. Hashmi, Angew. Chem. 1995, 107, 1749; Angew. Chem. Int. Ed. Engl. 1995, 34, 1581;
17. b) A. S. K. Hashmi, L. Schwarz, Chem. Ber./Recueil 1997, 130, 1449;
18. c) A. S. K. Hashmi, T. L. Ruppert, T. Knöfel, J. W. Bats, J. Org. Chem. 1997, 62, 7295;
19. d) A. S. K. Hashmi, J.-H. Choi, J. W. Bats, J. Prakt. Chem. 1999, 341, 342
20. A. S. K. Hashmi, L. Schwarz, M. Boite, Tetrahedron Lett. 1998, 39, 8969
21. M. Mühlstädt, J. Graefe, Chem. Ber. 1967, 100, 223; P. Cramer, T. T. Tidwell, J. Org. Chem. 1981,46, 2683; for the analogous reaction with alkynes, see: J. F. Arens, Adv. Org. Chem. 1960, 2, 163
22. M. Mühlstädt, J. Graefe, Chem. Ber. 1967, 100, 223; P. Cramer, T. T. Tidwell, J. Org. Chem. 1981,46, 2683; for the analogous reaction with alkynes, see: J. F. Arens, Adv. Org. Chem. 1960, 2, 163
23. M. Mühlstädt, J. Graefe, Chem. Ber. 1967, 100, 223; P. Cramer, T. T. Tidwell, J. Org. Chem. 1981,46, 2683; for the analogous reaction with alkynes, see: J. F. Arens, Adv. Org. Chem. 1960, 2, 163
24. 2O addition to alkynes: c) V. Jäger, H. G. Viehe in Methoden der Organischen Chemie (Houben-Weyl); Thieme Verlag: Stuttgart 1977; Vol. VII/2a, pp 726; J. S. Reichert, J. H. Bailey, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 1552; R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc., Perkin Trans. I 1976, 1983
25. 2O addition to alkynes: c) V. Jäger, H. G. Viehe in Methoden der Organischen Chemie (Houben-Weyl); Thieme Verlag: Stuttgart 1977; Vol. VII/2a, pp 726; J. S. Reichert, J. H. Bailey, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 1552; R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc., Perkin Trans. I 1976, 1983
26. 2O addition to alkynes: c) V. Jäger, H. G. Viehe in Methoden der Organischen Chemie (Houben-Weyl); Thieme Verlag: Stuttgart 1977; Vol. VII/2a, pp 726; J. S. Reichert, J. H. Bailey, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 1552; R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc., Perkin Trans. I 1976, 1983
27. 2O addition to alkynes: c) V. Jäger, H. G. Viehe in Methoden der Organischen Chemie (Houben-Weyl); Thieme Verlag: Stuttgart 1977; Vol. VII/2a, pp 726; J. S. Reichert, J. H. Bailey, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 1552; R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc., Perkin Trans. I 1976, 1983
28. 2O addition to alkynes: c) V. Jäger, H. G. Viehe in Methoden der Organischen Chemie (Houben-Weyl); Thieme Verlag: Stuttgart 1977; Vol. VII/2a, pp 726; J. S. Reichert, J. H. Bailey, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 1552; R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc., Perkin Trans. I 1976, 1983
29. Crystallographic data (excluding structure factors) for 8 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-132399. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code + (1223)36-033; e-mail: deposit@ chemcrys.cam.ac.uk).
30. a) A. Bax, M. F. Summers, J. Am. Chem. Soc. 1986, 108, 2093;
31. b) H. Kessler, M. Gehrke, C. Griesinger, Angew. Chem. 1988,100, 507; Angew. Chem. Int. Ed. Engl. 1988, 27, 490
32. b) H. Kessler, M. Gehrke, C. Griesinger, Angew. Chem. 1988,100, 507; Angew. Chem. Int. Ed. Engl. 1988, 27, 490
33. Y. Nagao, I.-Y. Jeong, W. S. Lee, S. Sano, J. Chem. Soc., Chem. Commun. 1996, 19
34. a) L. Brandsma, Preparative Acetylenic Chemistry, Elsevier, Amsterdam 1988, 35;
35. b) H. Hopf, I. Böhm, J. Kleinschroth, Org. Synth. 1981, 60, 41
36. L. S. Hegedus in Organometallics in Synthesis (Ed. M. Schlosser), John Wiley, Chichester 1994, p. 448
37. G. Sheldrick, Universität Göttingen 1996