Organotin hydride catalyzed carbon-carbon bond formation: Radical-mediated reductive cyclization of enals and enones

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 4-5

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

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002937546     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951827s     Document Type: Article

References (42)

1. For leading references, see: (a) Hart, D. J. Science 1984, 223, 883-887. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986. (c) Curran, D. P. Synthesis 1988, 417-439, 489-513. (d) Regitz, M.; Giese, B. Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1989. (e) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: New York, 1992.
2. For leading references, see: (a) Hart, D. J. Science 1984, 223, 883-887. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986. (c) Curran, D. P. Synthesis 1988, 417-439, 489-513. (d) Regitz, M.; Giese, B. Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1989. (e) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: New York, 1992.
3. For leading references, see: (a) Hart, D. J. Science 1984, 223, 883-887. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986. (c) Curran, D. P. Synthesis 1988, 417-439, 489-513. (d) Regitz, M.; Giese, B. Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1989. (e) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: New York, 1992.
4. For leading references, see: (a) Hart, D. J. Science 1984, 223, 883-887. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986. (c) Curran, D. P. Synthesis 1988, 417-439, 489-513. (d) Regitz, M.; Giese, B. Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1989. (e) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: New York, 1992.
5. For leading references, see: (a) Hart, D. J. Science 1984, 223, 883-887. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986. (c) Curran, D. P. Synthesis 1988, 417-439, 489-513. (d) Regitz, M.; Giese, B. Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1989. (e) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: New York, 1992.
6. For leading references, see: Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: Boston, 1987; Chapter 1.
7. (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
8. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
9. Corey, E. J.; Pyne, S. G. Tetrahedron Lett 1983, 24, 2821-2824. For a review, see: Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286
10. Corey, E. J.; Pyne, S. G. Tetrahedron Lett 1983, 24, 2821-2824. For a review, see: Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286
11. Early work: (a) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc 1986, 108, 5893-5901. (b) Ardisson, J.; Ferezou, J. P.; Julia, M.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 2001-2004. (c) Sugawara, T.; Otter, B. A.; Ueda, T. Tetrahedron Lett. 1988, 29, 75-78.
12. Early work: (a) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc 1986, 108, 5893-5901. (b) Ardisson, J.; Ferezou, J. P.; Julia, M.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 2001-2004. (c) Sugawara, T.; Otter, B. A.; Ueda, T. Tetrahedron Lett. 1988, 29, 75-78.
13. Early work: (a) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc 1986, 108, 5893-5901. (b) Ardisson, J.; Ferezou, J. P.; Julia, M.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 2001-2004. (c) Sugawara, T.; Otter, B. A.; Ueda, T. Tetrahedron Lett. 1988, 29, 75-78.
14. Enholm was the first to systematically explore the scope of this reaction: (a) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. (b) Enholm, E J.; Burroff, J. A. Tetrahedron Lett. 1992, 33, 1835-1838.
15. Enholm was the first to systematically explore the scope of this reaction: (a) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. (b) Enholm, E J.; Burroff, J. A. Tetrahedron Lett. 1992, 33, 1835-1838.
16. A polar variant of this strategy (catalytic tin hydride, stoichiometric silicon hydride) has been applied to the reduction of carbonyl groups. For an early report, see: Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. For a suggestion that radical-mediated reactions might be susceptible to this approach, see: Lipowitz, J.; Bowman, S. A. Aldrichim. Acta 1973, 6, 1-6.
17. A polar variant of this strategy (catalytic tin hydride, stoichiometric silicon hydride) has been applied to the reduction of carbonyl groups. For an early report, see: Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. For a suggestion that radical-mediated reactions might be susceptible to this approach, see: Lipowitz, J.; Bowman, S. A. Aldrichim. Acta 1973, 6, 1-6.
18. 3CN: Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304 (carbon-carbon bond-forming reactions).
19. 3CN: Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304 (carbon-carbon bond-forming reactions).
20. (a) Reference 7.
21. (b) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86.
22. (b) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86.
23. (c) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94.
24. (d) Bellegarde, B.; Pereyre, M.; Valade, J. Bull. Soc. Chim. Fr. 1967, 3082-3083.
25. For a mechanistic study, see: Pijselman, J.; Pereyre, M. J. Organomet. Chem. 1973, 63, 139-157.
26. For titanium-catalyzed reductive cyclization of δ,ε-unsaturated enals and enones to cyclopentanols: (a) Kablaoui, N.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788.
27. For titanium-catalyzed reductive cyclization of δ,ε-unsaturated enals and enones to cyclopentanols: (a) Kablaoui, N.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788.
28. 2O under otherwise identical conditions.
29. 2O provide yields and stereoselectivities essentially identical to those reported in Table 1.
30. 2O.
31. Preliminary efforts to employ polymethylhydrosiloxane (PMHS) as the stoichiometric reducing agent predominantly afforded uncyclized alcohol (1,2-reduction), along with small amounts (<25%) of the reductive cyclization product.
32. 3SnOEt.
33. 1H NMR).
34. We have not yet explored the generation of other ring sizes.
35. 3).
36. For example, see: (a) Conjugate reduction of α,β-unsaturated carbonyls: Pereyre, M.; Valade, J. Compt. Rend. 1965, 260, 581-584. (b) Reductive cyclization of keto-oximes: Naito, T., Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Conjugate reduction/intramolecular aldol: Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112-1113.
37. For example, see: (a) Conjugate reduction of α,β-unsaturated carbonyls: Pereyre, M.; Valade, J. Compt. Rend. 1965, 260, 581-584. (b) Reductive cyclization of keto-oximes: Naito, T., Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Conjugate reduction/intramolecular aldol: Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112-1113.
38. For example, see: (a) Conjugate reduction of α,β-unsaturated carbonyls: Pereyre, M.; Valade, J. Compt. Rend. 1965, 260, 581-584. (b) Reductive cyclization of keto-oximes: Naito, T., Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Conjugate reduction/intramolecular aldol: Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112-1113.
39. For example, see: (a) Conjugate reduction of α,β-unsaturated carbonyls: Pereyre, M.; Valade, J. Compt. Rend. 1965, 260, 581-584. (b) Reductive cyclization of keto-oximes: Naito, T., Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. (c) Conjugate reduction/intramolecular aldol: Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112-1113.
40. (a) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784-7785.
41. (b) Enholm, E. J.; Kinter, K. S. J. Org. Chem. 1995, 60, 4850-4855.
42. For example, see: Lee, E.; Tae, J. S.; Chong, Y. H.; Park, Y. C.; Yun, M.; Kim, S. Tetrahedron Lett. 1994, 35, 129-132.