Control of the regioselectivity in the Pauson-Khand reaction of 7- oxanorbornene derivatives

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7338-7341

  Arjona, Odón ^a   Csákÿ, Aurelio G ^a   Murcia, M Carmen ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BICYCLO COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0344604450     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9903095     Document Type: Article

References (22)

1. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977. For selected reviews, see: (a) Schore, N. E. Chem. Rev. 1988, 88, 1081. (b) Schore N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1037. (c) Geis, O.; Schmalz H-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
2. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977. For selected reviews, see: (a) Schore, N. E. Chem. Rev. 1988, 88, 1081. (b) Schore N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1037. (c) Geis, O.; Schmalz H-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
3. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977. For selected reviews, see: (a) Schore, N. E. Chem. Rev. 1988, 88, 1081. (b) Schore N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1037. (c) Geis, O.; Schmalz H-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
4. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977. For selected reviews, see: (a) Schore, N. E. Chem. Rev. 1988, 88, 1081. (b) Schore N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1037. (c) Geis, O.; Schmalz H-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
5. For selected reviews, see: (a) Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. (b) Woo, S.; Keay, B. A. Synthesis 1996, 669. (c) Chiu, P.; Lautens, M. Topics Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
6. For selected reviews, see: (a) Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. (b) Woo, S.; Keay, B. A. Synthesis 1996, 669. (c) Chiu, P.; Lautens, M. Topics Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
7. For selected reviews, see: (a) Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. (b) Woo, S.; Keay, B. A. Synthesis 1996, 669. (c) Chiu, P.; Lautens, M. Topics Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
8. For selected reviews, see: (a) Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. (b) Woo, S.; Keay, B. A. Synthesis 1996, 669. (c) Chiu, P.; Lautens, M. Topics Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
9. To the best of our knowledge, only one isolated example of the Pauson-Khand reaction of a bridgehead substituted 7-oxanorbornene derivative has been previously reported: de Meijere, A.; Wessjohan, L. Synlett 1990, 20.
10. (a) Vogel, P.; Fattori, D.; Gasparini, F.; le Drian, C. Synlett 1990, 173.
11. (b) Arjona, O.; de la Pradilla, R. F.; Pita-Romero, I.; Plumet, J.; Viso, A. Tetrahedron 1990, 46, 8199.
12. Arjona, O.; Domínguez, C.; de la Pradilla, R. F.; Mallo, A.; Manzano, C.; Plumet, J. J. Org. Chem. 1989, 54, 5883.
13. Arjona, O.; de Dios, A.; de la Pradilla, R. F.; Mallo, A.; Plumet, J. Tetrahedron 1990, 46, 8179.
14. Black, K. A.; Vogel, P. J. Org. Chem. 1986, 51, 5341.
15. 13C NMR spectra of all compounds 3 showed a chemical shift difference between the signals of C-2 and C-6 of 0.4-1.5 ppm, while this value was of 9-14 ppm for the regioisomeric compounds 4.
16. 2O). Finally, alcohols 3g,h and 4g,h have been oxidized to ketones 3a,c and 4a,c with PCC.
17. For the Pauson-Khand reactions of norborn-5-en-2-one and endo-norborn-5-en-2-ol with alkynes 2a and propyne, see: MacWhorter, S. E.; Sampath, V.; Olmstead, M. M.; Schore, N. J. Org. Chem. 1988, 53, 203.
18. The Pauson-Khand reaction of bromoethylene with 2a has been previously reported: Khand, I. U.; Pauson, P. L. J. Chem. Res. (M) 1977, 165. No regiochemical considerations are possible in this case. To the best of our knowledge, no further Pauson-Khand reactions of halogenated alkenes have been considered in the literature.
19. The enhancement of the regioselectivity in connection with a disminution in the chemical yield of the reaction may be attributed to unstability of adducts 3 under the thermal reaction conditions.
20. Otherwise the same product distribution (3:4 ratio) should have been obtained either starting from compounds 1 or the bromo derivatives 5 and 6.
21. For the intermediacy of hydridocobalt complexes in other Pauson-Khand related processes, see: (a) Montaña, A. M.; Moyano, A.; Pericàs, M. A.; Serratosa, F. Tetrahedron 1985, 41, 5995. (b) Billington, D. C.; Kerr, W. K.; Pauson, P. L.; Farnocchi, C. F. J. Organomet. Chem. 1988, 356, 213.
22. For the intermediacy of hydridocobalt complexes in other Pauson-Khand related processes, see: (a) Montaña, A. M.; Moyano, A.; Pericàs, M. A.; Serratosa, F. Tetrahedron 1985, 41, 5995. (b) Billington, D. C.; Kerr, W. K.; Pauson, P. L.; Farnocchi, C. F. J. Organomet. Chem. 1988, 356, 213.