Stereoselective synthesis of trisubstituted E-iodoalkenes by indium-catalyzed syn-addition of 1,3-dicarbonyi compounds to 1-iodoaikynes

Organic Letters

Volumn 10, Issue 6, 2008, Pages 1219-1221

  Tsuji, Hayato ^a   Fujimoto, Taisuke ^a   Endo, Kohei ^b   Nakamura, Masaharu ^c   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b WASEDA UNIVERSITY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 54949125891     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800105r     Document Type: Article

References (42)

1. (a) Kubota, K.; Nakamura, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2491-2493.
2. (b) Nakamura, M.; Hatakeyama, T.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 11820-11825.
3. (c) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 566-574.
4. (d) Rodriguez, A. L.; Bunlaksana-nusorn, T.; Knochel, P. Org. Lett. 2000, 2, 3285-3287.
5. (e) Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290-11291.
6. (f) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884-6885.
7. (a) Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002-13003.
8. (b) Nakamura, M.; Endo, K.; Nakamura, E. Org. Lett. 2005, 7, 3279-3281.
9. (c) Nakamura, M.; Endo, K.; Nakamura, E. Adv. Synth. Catal. 2005, 347, 1681-1686.
10. (d) Endo, K.; Hatakeyama, T.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 5264-5271.
11. (e) Tsuji, H.; Yamagata, K.-I.; Itoh, Y.; Endo, K.; Nakamura, M.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 8060-8062.
12. (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527.
13. (b) Staben, S. T.; Kennedy-Smith, J. J; Huang, D.; Corkey, B. K.; LaLonde, R. L.; Toste, F. D. Angew. Chem., Int. Ed. 2006, 45, 5991-5994.
14. (c) Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486-16487.
15. (d) Kuninobu, Y.; Kawata, A.; Takai, K. Org. Lett. 2005, 7, 4823-4825.
16. (e) Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 17168-17169.
17. (f) Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185-2188.
18. Horner-Wadsworth-Emmons-type reactions:
19. (a) Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87-99.
20. (b) Tago, K.; Kogen, H. J. Syn. Org. Chem. Jpn. 2001, 59, 971-984.
21. Transition-metal-catalyzed cross-coupling reactions:
22. (a) Tamao, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergaraon Press: Oxford. 1991; Vol. 3, p 435, and references therein,
23. (b) Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 481.
24. (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming. I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 521.
25. (d) Tonogaki, K.; Soga, K.; Itami, K.; Yoshida, J.-I. Synlelt 2005, 11, 1802-1804, and references cited therein.
26. Hydrometalation- and carbometalation-type addition reactions to alkynes:
27. (a) Normant, J. F.; Bourgain, M. Tetrahedron Lett. 1971. 12. 2583-2586.
28. (b) Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252-2254.
29. (c) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865.
30. (d) Marfat. A.; McGuirk, P. R.; Helquist, P.J. Org. Chem. 1979. 44, 3888-3901.
31. (e) Qian, M.; Huang, Z.; Negishi, E. Org. Lett. 2004, 6, 1531 - 1534.
32. (f) Pommier, A.; Stepanenko, V.; Jarowicki, K.; Kocienski, P. J. J. Org. Chem. 2003, 68, 4008-4013.
33. (g) Konno. T.; Daitoh, T.; Noiri, A.; Chae, J.; Ishihara, T.; Yamanaka, H. Org. Lett. 2004, 6, 933-936.
34. (h) Nishihara, Y.; Miyasaka, M.; Okamoto, M.; Takahashi, H.; Inoue, E.; Tanemura, K.; Takagi, K. J. Am. Chem. Soc. 2007, 129, 12634 12635.
35. For reviews of platform synthesis of multisubstituted alkenes:
36. (a) Itami, K.; Yoshida, J.-I. Bull. Chem. Soc.Jpn. 2006, 79, 811-824.
37. (b) Itami. K.; Yoshida, J.-I. Chem.-Eur. J. 2006, 12, 3966-3974.
38. Heck-type reactions:
39. (a) Biffis, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001, 173, 249-274. 34
40. (b) Knowles, J. P.; Whiting, A. Org. Biomol. Chem. 2007. 5, 31-44.
41. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
42. 2)3 (95.5 mg, 0.100 mmol) in toluene (2.0 ml,) was heated in the dark at 70 °C for 4 h. The mixture was filtered through a pad of silica gel and concentrated. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate = 95/5) to obtain the title compound as a yellow oil (655 mg. 88%). The yields on 100 mg runs averaged close to 92%.