Synthesis of benzo-fused lactams and lactones via Ru(II)-catalyzed cycloaddition of amide- and ester-tethered α,ω-diynes with terminal alkynes: Electronic directing effect of internal conjugated carbonyl group

Organic and Biomolecular Chemistry

Volumn 2, Issue 9, 2004, Pages 1287-1294

  Yamamoto, Yoshihiko ^a   Kinpara, Keisuke ^a   Saigoku, Tomoaki ^a   Nishiyama, Hisao ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMMONIUM COMPOUNDS; CATALYSIS; ESTERS; ISOMERS; PROTONS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

INTERNAL CONJUGATED CARBONYL GROUPS; REGIOCHEMISTRY; REGIOSELECTIVITY;

AROMATIC COMPOUNDS;

GADUS MORHUA;

EID: 2542472303     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b402649g     Document Type: Article

References (28)

1. N. E. Shore, in Comprehensive Organic Synthesis, eds. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, ch. 9.4, p. 1129; D. B. Grotjahn, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone, G. Wilkinson and L. S. Hegedus, Pergamon, Oxford, 1995, vol. 12, ch. 7.3, p. 741; H. Bönnemann and W. Brijoux, in Transition Metals for Organic Synthesis, eds. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 1998. vol. 1, 114.
2. N. E. Shore, in Comprehensive Organic Synthesis, eds. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, ch. 9.4, p. 1129; D. B. Grotjahn, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone, G. Wilkinson and L. S. Hegedus, Pergamon, Oxford, 1995, vol. 12, ch. 7.3, p. 741; H. Bönnemann and W. Brijoux, in Transition Metals for Organic Synthesis, eds. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 1998. vol. 1, 114.
3. N. E. Shore, in Comprehensive Organic Synthesis, eds. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, ch. 9.4, p. 1129; D. B. Grotjahn, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone, G. Wilkinson and L. S. Hegedus, Pergamon, Oxford, 1995, vol. 12, ch. 7.3, p. 741; H. Bönnemann and W. Brijoux, in Transition Metals for Organic Synthesis, eds. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 1998. vol. 1, 114.
4. S. Saito and Y. Yamamoto, Chem. Rev., 2000, 100, 2901.
5. Y. Yamamoto, R. Ogawa and K. Itoh, Chem. Commun., 2000, 549; Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143.
6. Y. Yamamoto, R. Ogawa and K. Itoh, Chem. Commun., 2000, 549; Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143.
7. S. M. Allin, C. J. Northfield, M. I. Page and A. M. Z. Slawin, J. Chem. Soc., Perkin Trans. 1, 2000, 1715; I. Takahashi and M. Hatanaka, Heterocycles, 1997, 45, 2475 and references cited therein.
8. S. M. Allin, C. J. Northfield, M. I. Page and A. M. Z. Slawin, J. Chem. Soc., Perkin Trans. 1, 2000, 1715; I. Takahashi and M. Hatanaka, Heterocycles, 1997, 45, 2475 and references cited therein.
9. Y. Lee, Y. Fujuwara, K. Ujita, M. Nagatomo, H. Ohta and I. Shimizu, Bull. Chem. Soc. Jpn., 2001, 74, 1437 and references cited therein.
10. D. M. Duckworth, S. Lee-Wong, A. M. Z. Slawin, E. H. Smith and D. J. Williams. J. Chem. Soc., Perkin Trans. 1, 1996, 815.
11. The Ni- and Rh-catalyzed cycloadditions of similar ester-diynes have been reported, see: Y. Sato, K. Ohashi and M. Mori, Tetrahedron Lett., 1999, 40, 5231; B. Witulski and A. Zimmermann, Synlett, 2002, 1855.
12. The Ni- and Rh-catalyzed cycloadditions of similar ester-diynes have been reported, see: Y. Sato, K. Ohashi and M. Mori, Tetrahedron Lett., 1999, 40, 5231; B. Witulski and A. Zimmermann, Synlett, 2002, 1855.
13. The major isomers were tentatively assigned to 16 in the light of the regioselectivity observed for other cases.
14. K. Kirchner, M. J. Calhorda, R. Schmid and L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721.
15. M. Paneque, M. L. Poveda, N. Rendón and K. Mereiter, J. Am. Chem. Soc., 2004, 126, 1610.
16. E. Valencia, A. J. Freyer and M. Shamma, Tetrahedron Lett., 1984, 25, 599.
17. R. Alonso, L. Castedo and D. Domínguez. Tetrahedron Lett., 1985, 26, 2925.
18. W. M. Whaley and T. R. Govindachan, Org. React., 1951, 6, 74.
19. N. Oshima, H. Suzuki and Y. Moro-oka, Chem. Lett., 1984. 1161.
20. J. Kong, C. A. White, A. I. Krylov, D. Sherrill. R. D. Adamson, T. R. Furlani, M. S. Lee, A. M. Lee, S. R. Gwaltney, T. R. Adams, C. Ochsenfeld, A. T. B. Gilbert, G. S. Kedziora, V. A. Rassolov, D. R. Maurice, N. Nair, Y. Shao, N. A. Besley, P. E. Maslen, J. P. Dombroski, H. Daschel, W. Zhang, P. P. Korambath, J. Baker, E. F. C. Byrd, T. V. Voorhis, M. Oumi, S. Hirata, C.-P. Hsu, N. Ishikawa, J. Florian, A. Warshel, B. G. Johnson, P. M. W. Gill. M. Head-Gordon and J. A. Pople, J. Comp. Chem., 2000, 21, 1532.
21. Spartan '02, version 1.0.2, Wavefunction. Inc., Irvine, CA, 2002.
22. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98 (Revision A.11). Gaussian, Inc., Pittsburgh, PA, 2001.
23. W. Kohn, A. D. Becke and R. G. Parr, J. Phys. Chem., 1996, 100, 12974.
24. P. J. Stephen, F. J. Devlin, C. F. Chabalowski and M. J. Frisch, Phys. Chem. Lett., 1994, 98, 11623.
25. W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Ther. Chim. Acta, 1973, 28, 213: M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 1982, 77, 3654.
26. W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Ther. Chim. Acta, 1973, 28, 213: M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 1982, 77, 3654.
27. W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Ther. Chim. Acta, 1973, 28, 213: M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 1982, 77, 3654.
28. E. D. Glendening, A. E. Reed, J. E. Carpenter and F. Weinhold, Gaussian NBO, version 3.1, Gaussian Inc., Pittsburgh PA, 2001.