Synthesis of functionalized olefins by cross and ring-closing metatheses [7]

Journal of the American Chemical Society

Volumn 122, Issue 15, 2000, Pages 3783-3784

  Chatterjee, Arnab K ^a   Morgan, John P ^a   Scholl, Matthias ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; FUNCTIONAL GROUP; KETONE DERIVATIVE; RUTHENIUM DERIVATIVE;

CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; LETTER; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0034685462     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9939744     Document Type: Letter

References (30)

1. For a recent review of olefin metathesis see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
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8. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
9. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
10. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
11. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
12. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
13. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
14. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
15. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
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17. Recent developments in cross-metathesis include: (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120. (c) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446. (d) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430. (e) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Miura, K.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1091-1094. (f) Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408-5412. (g) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558. (h) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 7, 773-788. (i) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (j) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
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19. Scholl, M.; Ding, S.; Lee C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956. The dimethylvinyl carbene 3 is prepared by analogy to the synthesis of the benzylidene reported therein. Details are included in the Supporting Information.
20. Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753.
21. 4j This result is also consistent with previous experiments which indicate that the propagating species, the methylidene derivative of 3, has a lifetime in excess of 12 hours: Ulman, M.; Grubbs, R. H. Unpublished results.
22. Ulman, M.; Belderrain, T. R.; Grubbs, R. H. Manuscript in preparation.
23. 2Me).
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28. 1H NMR.
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