Synthesis of tricyclic aromatic compounds by the intramolecular Pauson- Khand reaction promoted by molecular sieves

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3513-3519

  Pérez Serrano, Leticia ^a   Blanco Urgoiti, Jaime ^a   Casarrubios, Luis ^a   Domínguez, Gema ^a   Pérez Castells, Javier ^a  

^a UNIVERSIDAD SAN PABLO CEU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

TRICYCLIC AROMATIC COMPOUND;

ARTICLE; COMPLEX FORMATION; ISOMERISM; MOLECULAR INTERACTION; SPAIN; SYNTHESIS;

EID: 0034595752     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0001232     Document Type: Article

References (67)

1. For a preliminary communication of part of this work sec: (a) Blanco-Urgoiti, J.; Casarrubios, L.; Pérez-Castells, J. Tetrahedron Lett. 1999, 40, 2817-2820. (b) Pérez-Serrano, L.; Casarrubios, L.; Dominguez, G.; Pérez-Castells, J. Org. Lett. 1999, 1, 1187.
2. For a preliminary communication of part of this work sec: (a) Blanco-Urgoiti, J.; Casarrubios, L.; Pérez-Castells, J. Tetrahedron Lett. 1999, 40, 2817-2820. (b) Pérez-Serrano, L.; Casarrubios, L.; Dominguez, G.; Pérez-Castells, J. Org. Lett. 1999, 1, 1187.
3. For recent reviews on the Pauson-Khand reaction see: (a) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Ingate, S. T.; Marco-Contelles, J. Org. Proc. Prepr. Int. 1998, 123. (c) Mukai, Ch.; Hanaoka, M. Synlett 1996, 11. (d) Shore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, p 703. (e) Shore, N. E. In Comprehensive Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 1037. (f) Shore, N. E. Org. React. 1991, 40, 1.
4. For recent reviews on the Pauson-Khand reaction see: (a) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Ingate, S. T.; Marco-Contelles, J. Org. Proc. Prepr. Int. 1998, 123. (c) Mukai, Ch.; Hanaoka, M. Synlett 1996, 11. (d) Shore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, p 703. (e) Shore, N. E. In Comprehensive Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 1037. (f) Shore, N. E. Org. React. 1991, 40, 1.
5. For recent reviews on the Pauson-Khand reaction see: (a) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Ingate, S. T.; Marco-Contelles, J. Org. Proc. Prepr. Int. 1998, 123. (c) Mukai, Ch.; Hanaoka, M. Synlett 1996, 11. (d) Shore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, p 703. (e) Shore, N. E. In Comprehensive Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 1037. (f) Shore, N. E. Org. React. 1991, 40, 1.
6. For recent reviews on the Pauson-Khand reaction see: (a) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Ingate, S. T.; Marco-Contelles, J. Org. Proc. Prepr. Int. 1998, 123. (c) Mukai, Ch.; Hanaoka, M. Synlett 1996, 11. (d) Shore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, p 703. (e) Shore, N. E. In Comprehensive Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 1037. (f) Shore, N. E. Org. React. 1991, 40, 1.
7. For recent reviews on the Pauson-Khand reaction see: (a) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Ingate, S. T.; Marco-Contelles, J. Org. Proc. Prepr. Int. 1998, 123. (c) Mukai, Ch.; Hanaoka, M. Synlett 1996, 11. (d) Shore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, p 703. (e) Shore, N. E. In Comprehensive Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 1037. (f) Shore, N. E. Org. React. 1991, 40, 1.
8. For recent reviews on the Pauson-Khand reaction see: (a) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Ingate, S. T.; Marco-Contelles, J. Org. Proc. Prepr. Int. 1998, 123. (c) Mukai, Ch.; Hanaoka, M. Synlett 1996, 11. (d) Shore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, p 703. (e) Shore, N. E. In Comprehensive Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 1037. (f) Shore, N. E. Org. React. 1991, 40, 1.
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59. Coordination of heteroatoms to cobalt is thought to enhance yields in these reactions. See: (a) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (b) Kraft, M. E.; Juliano, C. A.; Scott, I. L.; Wright, C.; McEaching, M. D. J. Am. Chem. Soc. 1991, 113, 1693. Also intermolecular reactions with vinyl ethers and esters have recently been described: Kerr, W. J.; McLaughlin, M.; Pauson, P. L.; Robertson, S. M. Chem. Commun. 1999, 2171.
60. Coordination of heteroatoms to cobalt is thought to enhance yields in these reactions. See: (a) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (b) Kraft, M. E.; Juliano, C. A.; Scott, I. L.; Wright, C.; McEaching, M. D. J. Am. Chem. Soc. 1991, 113, 1693. Also intermolecular reactions with vinyl ethers and esters have recently been described: Kerr, W. J.; McLaughlin, M.; Pauson, P. L.; Robertson, S. M. Chem. Commun. 1999, 2171.
61. The interrupted Pauson-Khand reaction was first reported by Kraft involving the oxidation of the primary cyclization product. See: Kraft, M. E.; Wilson, A. M.; Dasse, O. A.; Shao, B.; Chung, Y. Y.; Fu, Z.; Bonaga, L. V. R.; Mollmann, M. K. J. Am. Chem. Soc. 1996, 118, 6080.
62. These allyl complexes are known in the literature and have found synthetic applications: (a) Kraft, M. E.; Pankowski, J. Tetrahedron Lett. 1990, 31, 5139. (b) Barinelli, L. S.; Li, Z.; Nicholas, K. M. Organometallics 1989, 8, 2474. (c) Hegedus, L. S.; Perry, R. J. J. Org. Chem. 1984, 49, 2570.
63. These allyl complexes are known in the literature and have found synthetic applications: (a) Kraft, M. E.; Pankowski, J. Tetrahedron Lett. 1990, 31, 5139. (b) Barinelli, L. S.; Li, Z.; Nicholas, K. M. Organometallics 1989, 8, 2474. (c) Hegedus, L. S.; Perry, R. J. J. Org. Chem. 1984, 49, 2570.
64. These allyl complexes are known in the literature and have found synthetic applications: (a) Kraft, M. E.; Pankowski, J. Tetrahedron Lett. 1990, 31, 5139. (b) Barinelli, L. S.; Li, Z.; Nicholas, K. M. Organometallics 1989, 8, 2474. (c) Hegedus, L. S.; Perry, R. J. J. Org. Chem. 1984, 49, 2570.
65. Castro, J.; Moyano, A.; Pericàs, M.; Riera, A. Tetrahedron 1995, 51, 6541.
66. 1H NMR spectra of these two cobalt complexes were compared with that of the cobalt hexacarbonyl complex of 2a. See Experimental Section.
67. Phosphorus ylide was generated by stirring the corresponding (1.50 mmol) phosphonium salt with (1.30 mmol) BuLi (1.6 M in hexane), KHMDS (0.5 M in toluene), or NaOH (phase-transfer conditions) for 30 min.