Macrocarbocycle synthesis by copper-and silver-mediated cyclization of tethered cyclopropenone acetals. Electronic tuning of metal vinylcarbene complex into vinylmetallic species

Organic Letters

Volumn 1, Issue 3, 1999, Pages 407-409

  Yu, Yong ^a   Yamanaka, Masahiro ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038275448     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990053p     Document Type: Article

References (29)

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5. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136. Trost, B. M.; Michellys, P. Y.; Gerusz, V. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1753. Brody, M. S.; Williams, R. M.; Finn, M. G. J. Am. Chem. Soc. 1997, 119, 3429-3433. (e) Doyle, M. P.; Peterson, C. S.; Protopopova, M. N.; Marnett, A. B.; Parker, D. L.; Ene, D. G.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 8826-8837.
6. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136. Trost, B. M.; Michellys, P. Y.; Gerusz, V. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1753. Brody, M. S.; Williams, R. M.; Finn, M. G. J. Am. Chem. Soc. 1997, 119, 3429-3433. (e) Doyle, M. P.; Peterson, C. S.; Protopopova, M. N.; Marnett, A. B.; Parker, D. L.; Ene, D. G.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 8826-8837.
7. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136. Trost, B. M.; Michellys, P. Y.; Gerusz, V. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1753. Brody, M. S.; Williams, R. M.; Finn, M. G. J. Am. Chem. Soc. 1997, 119, 3429-3433. (e) Doyle, M. P.; Peterson, C. S.; Protopopova, M. N.; Marnett, A. B.; Parker, D. L.; Ene, D. G.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 8826-8837.
8. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136. Trost, B. M.; Michellys, P. Y.; Gerusz, V. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1753. Brody, M. S.; Williams, R. M.; Finn, M. G. J. Am. Chem. Soc. 1997, 119, 3429-3433. (e) Doyle, M. P.; Peterson, C. S.; Protopopova, M. N.; Marnett, A. B.; Parker, D. L.; Ene, D. G.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 8826-8837.
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10. (a) Binger, P.; Müller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610-611. (b) Flatt, B. T.; Grubbs, R. H. Organometallics 1994, 13, 2728-2732.
11. (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. Stechl, H. M.; Chem. Ber. 1964, 97, 2681-2688.
12. (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. Stechl, H. M.; Chem. Ber. 1964, 97, 2681-2688.
13. (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. Stechl, H. M.; Chem. Ber. 1964, 97, 2681-2688.
14. Müller, P.; Granicher, C. Gazz. Chim. Ital. 1995, 125, 459-463.
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16. 6.
17. Elvidge, J. A.; Ralph, P. D. J. Chem. Soc. C 1966, 387-389.
18. 8E as a white solid (290 mg, 88% yield), mp 87-88°C. (11) Conditions for achieving effective bimolecular coupling reaction were found to need further optimization, which is under current investigations.
19. Nakamura, E.; Yu, Y.; Mori, S.; Yamago, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 374-376.
20. (a) Whitesides, G. M.; Casey, C. P.; Krieger, J. K. J. Am. Chem. Soc. 1971, 93, 1379-1389. (b) Kauffmann, T.; Sahm, W. Angew. Chem., Int. Ed. Engl. 1967, 6, 85.
21. (a) Whitesides, G. M.; Casey, C. P.; Krieger, J. K. J. Am. Chem. Soc. 1971, 93, 1379-1389. (b) Kauffmann, T.; Sahm, W. Angew. Chem., Int. Ed. Engl. 1967, 6, 85.
22. s symmetry. The 6-31G* basis set was used for C, H, and O and all electron Ahlrichs-SVP (Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577) for Cu: Nakamura, E.; Mori, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4887-4899.
23. s symmetry. The 6-31G* basis set was used for C, H, and O and all electron Ahlrichs-SVP (Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577) for Cu: Nakamura, E.; Mori, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4887-4899.
24. 3D pictures and coordinates of A and B are available on: http:// www.chem.s.u-tokyo.ac.jp/∼common/Theo/macro/title.html.
25. Boys, S. F. In Quantum Theory of Atoms, Molecules, and the Solid State; Lowdin, P. O., Ed.; Academic Press: New York, 1968; pp 253-262.
26. Strong perturbation effects of the acetal group have been observed also for free vinyl carbene species (Boger, D. L.; Brotherton, C. E. In Advances in Cycloaddition, volume 2; Curran, D. P., Ed.; JAI Press: Greenwich, 1990; p 147. Tokuyama, H.; Isaka, M.; and Nakamura, E. J. Am. Chem. Soc. 1992, 114, 5523) and trimethylenemethane species (Nakamura, E.; Yamago, S.; Ejiri, S.; Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 3183-3184. Nakamura, E. In Organic Synthesis in Japan. Past, Present and Future; Noyori, R., Ed.; Kagaku Dojin: Tokyo, 1992).
27. Strong perturbation effects of the acetal group have been observed also for free vinyl carbene species (Boger, D. L.; Brotherton, C. E. In Advances in Cycloaddition, volume 2; Curran, D. P., Ed.; JAI Press: Greenwich, 1990; p 147. Tokuyama, H.; Isaka, M.; and Nakamura, E. J. Am. Chem. Soc. 1992, 114, 5523) and trimethylenemethane species (Nakamura, E.; Yamago, S.; Ejiri, S.; Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 3183-3184. Nakamura, E. In Organic Synthesis in Japan. Past, Present and Future; Noyori, R., Ed.; Kagaku Dojin: Tokyo, 1992).
28. Strong perturbation effects of the acetal group have been observed also for free vinyl carbene species (Boger, D. L.; Brotherton, C. E. In Advances in Cycloaddition, volume 2; Curran, D. P., Ed.; JAI Press: Greenwich, 1990; p 147. Tokuyama, H.; Isaka, M.; and Nakamura, E. J. Am. Chem. Soc. 1992, 114, 5523) and trimethylenemethane species (Nakamura, E.; Yamago, S.; Ejiri, S.; Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 3183-3184. Nakamura, E. In Organic Synthesis in Japan. Past, Present and Future; Noyori, R., Ed.; Kagaku Dojin: Tokyo, 1992).
29. Strong perturbation effects of the acetal group have been observed also for free vinyl carbene species (Boger, D. L.; Brotherton, C. E. In Advances in Cycloaddition, volume 2; Curran, D. P., Ed.; JAI Press: Greenwich, 1990; p 147. Tokuyama, H.; Isaka, M.; and Nakamura, E. J. Am. Chem. Soc. 1992, 114, 5523) and trimethylenemethane species (Nakamura, E.; Yamago, S.; Ejiri, S.; Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 3183-3184. Nakamura, E. In Organic Synthesis in Japan. Past, Present and Future; Noyori, R., Ed.; Kagaku Dojin: Tokyo, 1992).