Samarium Diiodide-Mediated Reaction Of Organic Halides With Carbonyl Compounds

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 56, Issue 11, 1998, Pages 908-918

  Utimoto, Kiitiro ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542675373     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.56.908     Document Type: Article

References (46)

1. Girard, P.; Namy, J.L.; Kagan, H.B. J. Am. Chem. Soc. 1980, 102, 2693.
2. Kagan, H.B. New J. Chem. 1990, 14, 453; Molander, G.A. Chem. Rev. 1992, 92, 29; Molander, G.A.; Harris, C.R. ibid. 1996, 96, 307.
3. Kagan, H.B. New J. Chem. 1990, 14, 453; Molander, G.A. Chem. Rev. 1992, 92, 29; Molander, G.A.; Harris, C.R. ibid. 1996, 96, 307.
4. Kagan, H.B. New J. Chem. 1990, 14, 453; Molander, G.A. Chem. Rev. 1992, 92, 29; Molander, G.A.; Harris, C.R. ibid. 1996, 96, 307.
5. Inanaga, J.; Ujikawa, O.; Handa, Y.; Otsubo, K.; Yamaguchi, M. J. Alloys Comp. 1993, 192, 197.
6. 2O. a) Kagan, H. B.; Collin, J.; Namy, J. L.; Bied, C.; Dallemer, F.; Lebrun, A. J. Alloys Comp. 1993, 192, 191. b) Namy, J. L.; Collin, J.; Bied, C.; Kagan, H.B. Synlett 1992, 733. c) Under an influence of HMPA: Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485; Curran, D.P.; Fevig, D.P.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
7. 2O. a) Kagan, H. B.; Collin, J.; Namy, J. L.; Bied, C.; Dallemer, F.; Lebrun, A. J. Alloys Comp. 1993, 192, 191. b) Namy, J. L.; Collin, J.; Bied, C.; Kagan, H.B. Synlett 1992, 733. c) Under an influence of HMPA: Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485; Curran, D.P.; Fevig, D.P.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
8. 2O. a) Kagan, H. B.; Collin, J.; Namy, J. L.; Bied, C.; Dallemer, F.; Lebrun, A. J. Alloys Comp. 1993, 192, 191. b) Namy, J. L.; Collin, J.; Bied, C.; Kagan, H.B. Synlett 1992, 733. c) Under an influence of HMPA: Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485; Curran, D.P.; Fevig, D.P.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
9. 2O. a) Kagan, H. B.; Collin, J.; Namy, J. L.; Bied, C.; Dallemer, F.; Lebrun, A. J. Alloys Comp. 1993, 192, 191. b) Namy, J. L.; Collin, J.; Bied, C.; Kagan, H.B. Synlett 1992, 733. c) Under an influence of HMPA: Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485; Curran, D.P.; Fevig, D.P.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
10. Matsubara, S.; Yoshioka, M.; Utimoto, K. Angew. Chem. Int. Ed. Engl. 1997, 36, 617.
11. Aggawal, V.K. Angew. Chem. Int. Ed. Engl. 1994, 33, 175; Knochel, P. ibid. 1992, 31, 1459; Hoope, D.; Hense, T. Angew. Chem. Int. Ed. Engl. 1997, 56, 2282; Beak, P.; Basu, A.; Gallagher, D.J.; Park, Y.S.; Thayumanavan, S.; Acc. Chem. Res. 1996, 29, 552.
12. Aggawal, V.K. Angew. Chem. Int. Ed. Engl. 1994, 33, 175; Knochel, P. ibid. 1992, 31, 1459; Hoope, D.; Hense, T. Angew. Chem. Int. Ed. Engl. 1997, 56, 2282; Beak, P.; Basu, A.; Gallagher, D.J.; Park, Y.S.; Thayumanavan, S.; Acc. Chem. Res. 1996, 29, 552.
13. Aggawal, V.K. Angew. Chem. Int. Ed. Engl. 1994, 33, 175; Knochel, P. ibid. 1992, 31, 1459; Hoope, D.; Hense, T. Angew. Chem. Int. Ed. Engl. 1997, 56, 2282; Beak, P.; Basu, A.; Gallagher, D.J.; Park, Y.S.; Thayumanavan, S.; Acc. Chem. Res. 1996, 29, 552.
14. Aggawal, V.K. Angew. Chem. Int. Ed. Engl. 1994, 33, 175; Knochel, P. ibid. 1992, 31, 1459; Hoope, D.; Hense, T. Angew. Chem. Int. Ed. Engl. 1997, 56, 2282; Beak, P.; Basu, A.; Gallagher, D.J.; Park, Y.S.; Thayumanavan, S.; Acc. Chem. Res. 1996, 29, 552.
15. Hoffmann, R.W.; Bewersdorf, M. Angew. Chem. Int. Ed. Engl. 1988, 27, 1176; Hoffmann, R.W.; Kusche, D. Chem. Ber. 1994, 127, 1311; Schulze, V.; Brönstrup, M.; Böhm, V.P.W.; Schwordtfezen, P.; Scheczed, M.; Hoffmann, R.W. Angew. Chem. Int. Ed. Engl. 1998, 37, 824.
16. Hoffmann, R.W.; Bewersdorf, M. Angew. Chem. Int. Ed. Engl. 1988, 27, 1176; Hoffmann, R.W.; Kusche, D. Chem. Ber. 1994, 127, 1311; Schulze, V.; Brönstrup, M.; Böhm, V.P.W.; Schwordtfezen, P.; Scheczed, M.; Hoffmann, R.W. Angew. Chem. Int. Ed. Engl. 1998, 37, 824.
17. Hoffmann, R.W.; Bewersdorf, M. Angew. Chem. Int. Ed. Engl. 1988, 27, 1176; Hoffmann, R.W.; Kusche, D. Chem. Ber. 1994, 127, 1311; Schulze, V.; Brönstrup, M.; Böhm, V.P.W.; Schwordtfezen, P.; Scheczed, M.; Hoffmann, R.W. Angew. Chem. Int. Ed. Engl. 1998, 37, 824.
18. 2: Imamoto, T.; Takeyama, T.; Koto, H. Tetrahedron Lett. 1986, 27, 3243; Tabuchi, T.; Inanaga, J.; Yamaguchi, M.; ibid. 1986, 27, 3891.
19. 2: Imamoto, T.; Takeyama, T.; Koto, H. Tetrahedron Lett. 1986, 27, 3243; Tabuchi, T.; Inanaga, J.; Yamaguchi, M.; ibid. 1986, 27, 3891.
20. 2: 2.0 mmol); 47% (99 / 1) (1.0 mmol, 2.0 mmol, 4.0 mmol); 62% (1.0 mmol, 3.0 mmol, 6.0 mmol). In the case of the use of excess reagent, 1-iodo-2-phenylpropane and 2,5-diphenyl-3-hexene were observed as byproducts. The reduction of diastereotopic iodide may not proceed selectively and unfavored intermdiate decomposed into these by-products.
21. 2 did not afford halohydrine. A reduction of aldehyde into alcohol was detected. An addition of catalytic amount of Co(II) compound allowed the addition to proceed and gave iodohydrin with syn selectivity: Yoshioka, M.; Horiuchi, M.; Matsubara, S.; Utimoto, K. unpublished results.
22. 2-chiral aldehyde complex system or by facile racemization of α-iodoalkylsamarium species under the reaction with chiral aldehyde.
23. Kasuga, Y.; Matsubara, S.; Utimoto, K. Synlett 1998, in press.
24. Nakatsukasa, S.; Takai, K.; Utimoto, K. J. Org. Chem. 1986, 51, 5045; McDougal, P.G.; Condon, B.D.; Laffosse Jr., M.D.; Lauro, A.M.; Van Derveer, D.Tetrahedron Lett. 1988, 29, 2547; McDougal, P.G.; Condon, B.D. ibid. 1989, 30, 789; Ritter, R.H.; Cohen, T. J. Ant. Chem. Soc. 1986, 108, 3718; Kaiser, B.; Hoppe, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 323; Chandrasekhar, S.; Yu, J.; Falck, J.R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
25. Nakatsukasa, S.; Takai, K.; Utimoto, K. J. Org. Chem. 1986, 51, 5045; McDougal, P.G.; Condon, B.D.; Laffosse Jr., M.D.; Lauro, A.M.; Van Derveer, D.Tetrahedron Lett. 1988, 29, 2547; McDougal, P.G.; Condon, B.D. ibid. 1989, 30, 789; Ritter, R.H.; Cohen, T. J. Ant. Chem. Soc. 1986, 108, 3718; Kaiser, B.; Hoppe, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 323; Chandrasekhar, S.; Yu, J.; Falck, J.R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
26. Nakatsukasa, S.; Takai, K.; Utimoto, K. J. Org. Chem. 1986, 51, 5045; McDougal, P.G.; Condon, B.D.; Laffosse Jr., M.D.; Lauro, A.M.; Van Derveer, D.Tetrahedron Lett. 1988, 29, 2547; McDougal, P.G.; Condon, B.D. ibid. 1989, 30, 789; Ritter, R.H.; Cohen, T. J. Ant. Chem. Soc. 1986, 108, 3718; Kaiser, B.; Hoppe, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 323; Chandrasekhar, S.; Yu, J.; Falck, J.R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
27. Nakatsukasa, S.; Takai, K.; Utimoto, K. J. Org. Chem. 1986, 51, 5045; McDougal, P.G.; Condon, B.D.; Laffosse Jr., M.D.; Lauro, A.M.; Van Derveer, D.Tetrahedron Lett. 1988, 29, 2547; McDougal, P.G.; Condon, B.D. ibid. 1989, 30, 789; Ritter, R.H.; Cohen, T. J. Ant. Chem. Soc. 1986, 108, 3718; Kaiser, B.; Hoppe, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 323; Chandrasekhar, S.; Yu, J.; Falck, J.R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
28. Nakatsukasa, S.; Takai, K.; Utimoto, K. J. Org. Chem. 1986, 51, 5045; McDougal, P.G.; Condon, B.D.; Laffosse Jr., M.D.; Lauro, A.M.; Van Derveer, D.Tetrahedron Lett. 1988, 29, 2547; McDougal, P.G.; Condon, B.D. ibid. 1989, 30, 789; Ritter, R.H.; Cohen, T. J. Ant. Chem. Soc. 1986, 108, 3718; Kaiser, B.; Hoppe, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 323; Chandrasekhar, S.; Yu, J.; Falck, J.R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
29. Nakatsukasa, S.; Takai, K.; Utimoto, K. J. Org. Chem. 1986, 51, 5045; McDougal, P.G.; Condon, B.D.; Laffosse Jr., M.D.; Lauro, A.M.; Van Derveer, D.Tetrahedron Lett. 1988, 29, 2547; McDougal, P.G.; Condon, B.D. ibid. 1989, 30, 789; Ritter, R.H.; Cohen, T. J. Ant. Chem. Soc. 1986, 108, 3718; Kaiser, B.; Hoppe, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 323; Chandrasekhar, S.; Yu, J.; Falck, J.R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
30. Hoffmann, R.W.; Julius, M.; Chemla, F.; Frenzen, G. Tetrahedron 1994, 50, 6049; Hoffmann, R.W.; Dress, R.K.; Ruhland, T.; Wenzel, A. Chem. Ber., 1995, 128, 861.
31. Hoffmann, R.W.; Julius, M.; Chemla, F.; Frenzen, G. Tetrahedron 1994, 50, 6049; Hoffmann, R.W.; Dress, R.K.; Ruhland, T.; Wenzel, A. Chem. Ber., 1995, 128, 861.
32. Yamashita, M.; Kitagawa, K.; Ohhara, T.; Iida, Y.; Masumi, A.; Ohta, S. Chem. Lett. 1993, 653.
33. The reason for the failure of kinetic resolution was supposed that the intermediate 9 might form aggregates consisting from a pair of enantiomers. The ligation that breaks these aggregates makes the kinetic resolution possible; see text.
34. Soula, G. J. Org. Chem. 1995, 50, 3717.
35. Utimoto, K.; Takai, T.; Matsui, T.; Matsubara, S. Bull. Soc. Chim. Fr. 1997, 134, 365.
36. (a)Samarium-mediated reaction of bromoesters in THF; Park, H.S.; Lee, S.I.; Kim, Y.H. Tetrahedron Lett. 1996, 36, 1673.
37. (b) Samarium-mediated head-to-head coupling of bromoesters in THF-HMPA; Balaux, E.; Ruel, R.; Tetrahedron Lett. 1996, 37, 801.
38. Self-condensation of lithium enolate to produce β-keto ester; (a) Sullivan, D.F.; Woodbury, R.P.; Rathke, M.W.; J. Org. Chem. 1977, 42, 2038. (b) Rathke, M.W.; Sullivan, D. F.; J. Am. Chem. Soc. 1973, 95, 3050.
39. Self-condensation of lithium enolate to produce β-keto ester; (a) Sullivan, D.F.; Woodbury, R.P.; Rathke, M.W.; J. Org. Chem. 1977, 42, 2038. (b) Rathke, M.W.; Sullivan, D. F.; J. Am. Chem. Soc. 1973, 95, 3050.
40. Dianion of β-keto ester; Huckin, S.N.; Weiler, L. Can. J. Chem. 1974, 52, 2157.
41. The dianion, obtained from ethyl acetoacetate and lithium diisopropylamide, acted as a strong base to β-tetralone and resulted in an enolization.
42. β,δ-Diketo ester: (a) Yamaguchi, M.; Shibato, K.; Hirao I.; Chem. Lett. 1985, 1145. (b) Huckin, S.N.; Weiler, L. Can. J. Chem. 1973, 52, 1343. (c) Harris, T.M.; Harris, C.M.; Tetrahedron 1977, 33, 2159.
43. β,δ-Diketo ester: (a) Yamaguchi, M.; Shibato, K.; Hirao I.; Chem. Lett. 1985, 1145. (b) Huckin, S.N.; Weiler, L. Can. J. Chem. 1973, 52, 1343. (c) Harris, T.M.; Harris, C.M.; Tetrahedron 1977, 33, 2159.
44. β,δ-Diketo ester: (a) Yamaguchi, M.; Shibato, K.; Hirao I.; Chem. Lett. 1985, 1145. (b) Huckin, S.N.; Weiler, L. Can. J. Chem. 1973, 52, 1343. (c) Harris, T.M.; Harris, C.M.; Tetrahedron 1977, 33, 2159.
45. Coordination of an alkoxy group to a samarium reagent may accelerate the nucleophilic addition; Chen, X.; Hortelaro, E.R.; Eliel, E.L. J. Am. Chem. Soc. 1992, 107, 25.
46. Shibata, I.; Nisio, M.; Baba, A.; Matsuda, H.Chem. Lett., 1993, 1219.