Bu3SnH-Mediated Pinacol Coupling of 1,5- and 1,6-Dicarbonyl Compounds: Synthetic and Mechanistic Studies

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6375-6381

  Hays, David S ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000588661     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9809130     Document Type: Article

References (42)

1. (a) Neumann, W. P. Synthesis 1987, 665-683.
2. (b) RajanBabu, T. V. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995.
3. (c) Davies, A. G. Organotin Chemistry; VCH: New York, 1997.
4. (d) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: Boston, 1987.
5. Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893-5901.
6. Sugawara, T.; Otter, B. A.; Ueda, T. Tetrahedron Lett. 1988, 29, 75-78.
7. (a) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942.
8. (b) Enholm, E. J.; Burroff, J. A. Tetrahedron Lett. 1992, 33, 1835-1838.
9. 3SnH-mediated reductive cyclizations of carbonyl/oxime ethers, see: (a) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Naito, T.; Torieda, M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. Chem. Pharm. Bull. 1996, 44, 624-626. (d) Tormo, J.; Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 201-202.
10. 3SnH-mediated reductive cyclizations of carbonyl/oxime ethers, see: (a) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Naito, T.; Torieda, M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. Chem. Pharm. Bull. 1996, 44, 624-626. (d) Tormo, J.; Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 201-202.
11. 3SnH-mediated reductive cyclizations of carbonyl/oxime ethers, see: (a) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Naito, T.; Torieda, M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. Chem. Pharm. Bull. 1996, 44, 624-626. (d) Tormo, J.; Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 201-202.
12. 3SnH-mediated reductive cyclizations of carbonyl/oxime ethers, see: (a) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Naito, T.; Torieda, M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. Chem. Pharm. Bull. 1996, 44, 624-626. (d) Tormo, J.; Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 201-202.
13. For a comprehensive review of pinacol couplings, see: Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6.
14. We are not aware of any precedent for the addition of a tin ketyl to a carbonyl group.
15. For discussions concerning the intramolecular addition of a nonstabilized carbon-centered radical to a carbonyl group, see: (a) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116-2117. Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 123, 5791-5799. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 230-234. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 2674-2681. (c) Curran, D. P. Synthesis 1988, 417-439.
16. For discussions concerning the intramolecular addition of a nonstabilized carbon-centered radical to a carbonyl group, see: (a) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116-2117. Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 123, 5791-5799. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 230-234. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 2674-2681. (c) Curran, D. P. Synthesis 1988, 417-439.
17. For discussions concerning the intramolecular addition of a nonstabilized carbon-centered radical to a carbonyl group, see: (a) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116-2117. Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 123, 5791-5799. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 230-234. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 2674-2681. (c) Curran, D. P. Synthesis 1988, 417-439.
18. For discussions concerning the intramolecular addition of a nonstabilized carbon-centered radical to a carbonyl group, see: (a) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116-2117. Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 123, 5791-5799. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 230-234. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 2674-2681. (c) Curran, D. P. Synthesis 1988, 417-439.
19. For discussions concerning the intramolecular addition of a nonstabilized carbon-centered radical to a carbonyl group, see: (a) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116-2117. Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 123, 5791-5799. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 230-234. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 211, 2674-2681. (c) Curran, D. P. Synthesis 1988, 417-439.
20. For a recent study of the relative reactivity of oxygen-stabilized versus nonstabilized carbon radicals, see: Johnson, C. C.; Horner, J. H.; Tronche, C.; Newcomb, M. J. Am. Chem. Soc. 1995, 117, 1684-1687.
21. Yeung, B.-W. A.; Alonso, R.; Vite, G. D.; Fraser-Reid, B. J. Carbohydr. Chem. 1989, 8, 413-427.
22. For a preliminary report, see: Hays, D. S.; Fu, G. C. J. Am. Chem, Soc. 1995, 117, 7283-7284.
23. For reviews of the functionalization of 1,3-dioxa-2-stannolane, see: (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: Boston, 1987. (b) Blunden, S. J.; Cusack, P. A.; Smith, P. J. J. Organomet. Chem. 1987, 325, 141-152. (c) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643-663.
24. For reviews of the functionalization of 1,3-dioxa-2-stannolane, see: (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: Boston, 1987. (b) Blunden, S. J.; Cusack, P. A.; Smith, P. J. J. Organomet. Chem. 1987, 325, 141-152. (c) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643-663.
25. For reviews of the functionalization of 1,3-dioxa-2-stannolane, see: (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: Boston, 1987. (b) Blunden, S. J.; Cusack, P. A.; Smith, P. J. J. Organomet. Chem. 1987, 325, 141-152. (c) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643-663.
26. A related process involving a carbon-centered radical has been observed as a minor (≤10%) side reaction in the stannylformylation of 1,6-dienes: Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570-7571 and references therein.
27. (a) Davies has shown that the presence of electronegative substituents on tin facilitates homolytic displacement of an alkyl group by an alkoxy radical; for an overview, see: Chemistry of Tin; Harrison, P. G., Ed.; Chapman and Hall: New York, 1989.
28. (b) For a recent review of free-radical homolytic substitution, see: Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265-13314.
29. 3Sn transfer: Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669-670.
30. 3Sn transfer: Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669-670.
31. 3Sn transfer: Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669-670.
32. Vite, G. D.; Fraser-Reid, B. Synth. Commun. 1988, 18, 1339-1342.
33. H2 pathway, see: Alberti, A.; Dellonte, S.; Paradisi, C.; Roffia, S.; Pedulli, G. F. J. Am. Chem. Soc. 1990, 112, 1123-1129.
34. (b) For related work, see: Kulicke, K. J.; Chatgilialoglu, C.; Kopping, B.; Giese, B. Helv. Chim. Acta 1992, 75, 935-939. Miura, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2477-2478.
35. (b) For related work, see: Kulicke, K. J.; Chatgilialoglu, C.; Kopping, B.; Giese, B. Helv. Chim. Acta 1992, 75, 935-939. Miura, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2477-2478.
36. 3SiH.
37. Gmelin Handbook of Inorganic Chemistry, Organotin Compounds, 8th ed.; Kruerke, U., Ed.; Springer-Verlag: Berlin, 1988; Vol. 15, p 52.
38. (a) Reference 19.
39. (b) See also: Grindley, T. B.; Thangarasa, R. J. Am. Chem. Soc. 1990, 112, 1364-1373.
40. Basavaiah, D.; Pandiaraju, S.; Muthukumaran, K. Tetrahedron: Asymmetry 1996, 7, 13-16.
41. Cristol, S. J.; Franzus, B. J. Am. Chem. Soc. 1957, 79, 2488-2489.
42. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415-4416.