Domino ring-opening metathesis-ring-closing metathesis of bicyclo[2.2.2]octene derivatives: Scope and limitations

Journal of Organic Chemistry

Volumn 77, Issue 14, 2012, Pages 6345-6350

  Bose, Sritama ^a   Ghosh, Manju ^a   Ghosh, Subrata ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLIC SYSTEMS; DECALIN; REACTIVITY PATTERN; RING OPENING;

OLEFINS; ORGANIC SOLVENTS;

CLIMATE MODELS;

2 OXO 4',5' DIHYDRO 2'H SPIRO[BICYCLO[2.2.1]HEPT[5]ENE 2,3' FURAN] 4' CARBALDEHYDE; 4 (1,4 DIOXASPIRO[4.5]DECAN 2 YL) 6,9 VINYL 2 OXASPIRO[4.5]DECAN 1 ONE; 4 [1 (TERT BUTYLDIMETHYLSILYLOXY)BUT 3 ENYL] 6,9 DIVINYL 2 OXASPIRO[4.5]DECAN 1 ONE; 4' (1,2 DIHYDROXYETHYL) 1,4 DIVINYL 4',5' DIHYDRO 2'H SPIRO[BICYCLO[2.2.2]OCT[5]ENE 2,3' FURAN] 2' ONE; 4' (1,2 DIHYDROXYETHYL)DIHYDRO 2'H SPIRO[BICYCLO[2.2.2]OCTANE 2,3' FURAN] 2' ONE; 4' (1,4 DIOXASPIRO[4.5]DECAN 2 YL) 4',5' DIHYDRO 2'H SPIRO(BICYCLO[2.2.1]HEPT[5]ENE 2,3' FURAN) 2' ONE; 4' (1,4 DIOXASPIRO[4.5]DECAN 2 YL) 4',5' DIHYDRO 2'H SPIRO(BICYCLO[2.2.1]OCT[5]ENE 2,3' FURAN) 2' ONE; 4' (2 OXOBUT 3 ENYL) 4',5' DIHYDRO 2'H SPIRO[BICYCLO[2.2.2]OCT[5]ENE 2,3' FURAN] 2' ONE; 4' [1 (TERT BUTYLDIMETHYLSILYLOXY) 3 METHYLBUT 3 ENYL] 4',5' DIHYDRO 2'H SPIRO[BICYCLO[2.2.1]HEPT[5]ENE 2,3' FURAN] 2' ONE; 4' [1 (TERT BUTYLDIMETHYLSILYLOXY)BUT 3 ENYL] 4',5' DIHYDRO 2'H SPIRO[BICYCLO[2.2.1]HEPT[5]ENE 2,3' FURAN] 2' ONE; 4' [1 (TERT BUTYLDIMETHYLSILYLOXY)BUT 3 ENYL] 4',5' DIHYDRO 2'H SPIRO[BICYCLO[2.2.2]OCT[5]ENE 2,3' FURAN] 2' ONE; ALKENE; BICYCLO COMPOUND; BICYCLO[2.2.2]OCTENE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; NORBORNANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIELS ALDER REACTION; ISOMERIZATION; RING CLOSING METATHESIS; RING OPENING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

BICYCLO COMPOUNDS; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84864035567     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300945b     Document Type: Article

References (40)

1. Arjona, O.; Csaky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611
2. Holub, N.; Blechert, S. Chem. Asian J. 2007, 2, 1064
3. Malik, C. K.; Ghosh, S. Org. Lett. 2007, 9, 2537
4. Maity, S.; Ghosh, S. Tetrahedron Lett. 2008, 49, 1133
5. Mondal, S.; Malik, C. K.; Ghosh, S. Tetrahedron Lett. 2008, 49, 5649
6. Malik, C. K.; Yadav, R. N.; Drew, M. G. B.; Ghosh, S. J. Org. Chem. 2009, 74, 1957
7. Malik, C. K.; Hossain, Md. F.; Ghosh, S. Tetrahedron Lett. 2009, 50, 3063
8. Mondal, S.; Yadav, R. N.; Ghosh, S. Tetrahedron Lett. 2009, 50, 5277
9. Maity, S.; Ghosh, S. Tetrahedron 2009, 65, 9202
10. Matcha, K.; Maity, S.; Malik, C. K.; Ghosh, S. Tetrahedron Lett. 2010, 51, 2754
11. Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem. 1990, 55, 843
12. Stragies, R.; Blechert, S. Synlett 1998, 169
13. Arjona, O.; Csaky, A. G.; Murcia, M. C.; Plumet, J. Tetrahedron Lett. 2000, 41, 9777
14. Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828
15. Arjona, O.; Csaky, A. G.; Medel, R.; Plumet, J. J. Org. Chem. 2002, 67, 1380
16. Sakurai, H.; Daiko, T.; Hirao, T. Science 2003, 301, 1878
17. Arjona, O.; Csaky, A. G.; Leon, V.; Medel, R.; Plumet, J. Tetrahedron Lett. 2004, 45, 565
18. Chandler, C. L.; Phillips, A. J. Org. Lett. 2005, 7, 3493
19. Maechling, S.; Norman, S. E.; Mckendrick, J. E.; Basra, S.; Koppner, K.; Blechert, S. Tetrahedron Lett. 2006, 47, 189
20. Hart, A. C.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 1094
21. Phillips, A. J.; Hart, A. C.; Henderson, J. A. Tetrahedron Lett. 2006, 47, 3743
22. Calvet, G.; Blanchard, N.; Kouklovsky, C. Org. Lett. 2007, 9, 1485
23. Henderson, J. A.; Phillips, A. J. Angew. Chem., Int. Ed. 2008, 47, 8499
24. Hagiwara, H.; Katsumi, T.; Endou, S.; Hoshi, T.; Suzuki, T. Tetrahedron 2002, 58, 6651
25. Minger, T. L.; Phillips, A. J. Tetrahedron Lett. 2002, 43, 5357
26. Pfeiffer, M. W. B.; Phillips, A. J. J. Am. Chem. Soc. 2005, 127, 5334
27. For isolation, see: Karioti, A.; Skaltsa, H.; Linden, A.; Perozzo, R.; Brun, R.; Tasdemir, D. J. Org. Chem. 2007, 72, 8103
28. For synthesis, see: Li, Y.; Nawrat, C.; Pattenden, G.; Winne, M. J. Org. Biomol. Chem. 2009, 7, 639
29. Watanabe, H.; Yamaguchi, T.; Furuuchi, T.; Kitahara, T. Tetrahedron Lett. 2001, 42, 917
30. Fotiadu, F.; Michel, F.; Buono, G. Tetrahedron Lett. 1990, 31, 4863
31. Posner, G. H.; Nelson, T. D.; Kinter, C. M.; Johnson, N. J. Org. Chem. 1992, 57, 4083
32. Takeda, K.; Imaoka, I.; Yoshii, E. Tetrahedron 1994, 50, 10839
33. Ghatak, A.; Sarkar, S.; Ghosh, S. Tetrahedron 1997, 53, 17335
34. Maier, M. E.; Perez, C. Synlett 1998, 159
35. Richter, F.; Bauer, M.; Perez, C.; Maichle-Mössmer, C.; Maier, M. E. J. Org. Chem. 2002, 67, 2474
36. Nakamura, S.; Kikuchi, F.; Hashimoto, S. Angew. Chem., Int. Ed. 2008, 47, 7091
37. Ghosh, M.; Bose, S.; Maity, S.; Ghosh, S. Tetrahedron Lett. 2009, 50, 7102
38. Crystallographic data for compound 8 has been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 842082. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: +44 1223-336033. E-mail: deposit@ccdc.cam.ac.uk.
39. Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Org. Lett. 2001, 3, 2045
40. Alcaide, B.; Almendros, P.; Luna, A. Chem. Rev. 2009, 109, 3817