Regioselective ring-opening and cross-coupling metathesis of 2- substituted 7-oxanorbornenes. New stereoselective entry into trisubstituted tetrahydrofurans

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9739-9741

  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; NORBORNENE DERIVATIVE; RUTHENIUM DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343776189     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9913053     Document Type: Article

References (26)

1. 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. Top. Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
2. 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. Top. Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
3. 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. Top. Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
4. 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. Top. Curr. Chem. 1997, 190, 3. (d) Kappe, C. O.; Murphree, S.; Padwa, A. Tetrahedron 1997, 53, 14179.
5. For selected recent reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1988, 371.
6. For selected recent reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1988, 371.
7. (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611.
8. (b) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479.
9. For a recent account on the preferences of ring-closing metathesis on the synthesis of spirocyclic systems see: Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247.
10. Review: Ivin, K. J. Olefin Metathesis; Academic Press: London, 1996. For recent references see: (a) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784. (b) Ball, C. P.; Barrett, A. G. M.; Poitont, L. F.; Smith, M. L.; Thorn, Z. E. J. J. Chem. Soc., Chem. Commun. 1998, 2453. (c) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627.
11. Review: Ivin, K. J. Olefin Metathesis; Academic Press: London, 1996. For recent references see: (a) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784. (b) Ball, C. P.; Barrett, A. G. M.; Poitont, L. F.; Smith, M. L.; Thorn, Z. E. J. J. Chem. Soc., Chem. Commun. 1998, 2453. (c) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627.
12. Review: Ivin, K. J. Olefin Metathesis; Academic Press: London, 1996. For recent references see: (a) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784. (b) Ball, C. P.; Barrett, A. G. M.; Poitont, L. F.; Smith, M. L.; Thorn, Z. E. J. J. Chem. Soc., Chem. Commun. 1998, 2453. (c) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627.
13. Review: Ivin, K. J. Olefin Metathesis; Academic Press: London, 1996. For recent references see: (a) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784. (b) Ball, C. P.; Barrett, A. G. M.; Poitont, L. F.; Smith, M. L.; Thorn, Z. E. J. J. Chem. Soc., Chem. Commun. 1998, 2453. (c) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627.
14. To the best of our knowledge, only the ring-opening metathesis of 7-oxanorbornene derivatives with identical substitution at positions 2 and 3 has been previously reported: Schenider, M. F.; Lucas, N.; Velder, J. Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257
15. For the regioselectivity in electrophilic additions see: (a) Vogel, P.; Fattori, D.; Gasparini, F.; le Drian, C. Synlett 1990, 173. (b) Arjona, O.; de la Pradilla, R. F.; Pita-Romero, I.; Plumet, J.; Viso, A. Tetrahedron 1990, 46, 8199.
16. For the regioselectivity in electrophilic additions see: (a) Vogel, P.; Fattori, D.; Gasparini, F.; le Drian, C. Synlett 1990, 173. (b) Arjona, O.; de la Pradilla, R. F.; Pita-Romero, I.; Plumet, J.; Viso, A. Tetrahedron 1990, 46, 8199.
17. For the regioslectivity in 1,3-dipolar cycloadditions see: (a) Arjona, O.; Domínguez, C.; de la Pradilla, R. F.; Mallo, A.; Manzano, C.; Plumet, J. J. Org. Chem., 1989, 54, 5883. (b) Arjona, O.; de Dios, A.; de la Pradilla, R. F.; Mallo, A.; Plumet, J. Tetrahedron 1990, 46, 8179.
18. For the regioslectivity in 1,3-dipolar cycloadditions see: (a) Arjona, O.; Domínguez, C.; de la Pradilla, R. F.; Mallo, A.; Manzano, C.; Plumet, J. J. Org. Chem., 1989, 54, 5883. (b) Arjona, O.; de Dios, A.; de la Pradilla, R. F.; Mallo, A.; Plumet, J. Tetrahedron 1990, 46, 8179.
19. For the regioselectivity in Diels-Alder reactions see: Black, K. A.; Vogel, P. J. Org. Chem. 1986, 51, 5341.
20. For the regioselectivity in the Pauson-Khand reaction see: Arjona, O.; Csákÿ, A. G.; Murcia, M. C.; Plumet, J. J. Org. Chem. 1999, 64, 7338.
21. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2179.
22. Compounds 3 and 4 were obtained as mixtures of the corresponding E and Z alkenes.
23. The combination of cross, ring-opening, and ring-closing metathesis has been reported in the case of endo-2-substituted norborn-5-enes. See: Stragies, R.; Blechert, S. Synlett 1998, 169.
24. Compounds 5 and 6 were separated by GC or HPLC. The structural assignment of both regioisomers was based on the analysis of their MS fragmentation pattern. See the Supporting Information.
25. Hérisson, J. L.; Chauvin, Y. Makromol. Chem. 1970, 141, 161.
26. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711-1754.