Catalytic Enantioselective Iodocyclization of γ-Hydroxy-cis-alkenes

Journal of the American Chemical Society

Volumn 125, Issue 51, 2003, Pages 15748-15749

  Kang, Sung Ho ^a   Lee, Sung Bae ^a   Park, Chul Min ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; COMPLEX FORMATION; CYCLIZATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0346365076     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0369921     Document Type: Article

References (33)

1. (a) Rousseau, G.; Robin, S. Tetrahedron 1998, 54, 13681.
2. (b) Harding, K. E.; Tinger, T. H. In Comprehensive Organic Synthesis: Trost, B. M., Fleming, I., Eds.: Pergamon Press: Oxford, 1991; Vol. 4, p 463.
3. (c) Mulzer, J. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H. J., Braun, M., Krohn, K., Reissig, H. U., Eds.; VCH: Weinheim, 1991; p 157.
4. (a) Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175.
5. (b) Furth, M. J.; Brown, E. G. J. Am. Chem. Soc. 1987, 109, 6844.
6. (a) Back, T. G.; Dyck, B. P.; Nan, S. Tetrahedron 1999, 55, 3191.
7. (b) Nishibayashi, Y.: Srivastava, S. K.; Takada, H.; Fukuzawa, S.-I.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 2321.
8. (c) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726.
9. (d) Fujita, K.-I.; Iwaoka, M.; Tomoda, S. Chem. Lett. 1992, 1123.
10. (a) Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297.
11. (b) Grossman, R. B.; Trupp, R. J. Can. J. Chem. 1998, 76, 1233.
12. (a) Kitagawa, O.; Taguchi, T. Synlett 1999, 1191.
13. (b) Kitagawa, O.; Hanano, T.; Tanabe, K.; Shiro, M.; Taguchi, T. J. Chem. Soc., Chem. Commun. 1992, 1005.
14. (a) El-Qisairi, A. K.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790
15. , (b) El-Qisairi; A. K.; Qaseer, H. A.; Katsigras, G.; Lorenzi, P.; Trivedi, U.; Tracz, S.; Hartman, A.; Miller, J. A.; Henry, P. M. Org. Lett. 2003, 5, 439.
16. (a) Grundon, M. F.; Stewart, D.; Watts, W. E. J. Chem. Soc., Chem. Commun. 1973, 573.
17. (b) Carlson, R. M.; Funk, A. H. Tetrahedron Lett. 1971, 3661.
18. Kang, S. H.; Kim, M. J. Am. Chem. Soc. 2003, 125, 4684.
19. Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5891.
20. Leung, W.-H.; Chan, E. Y. Y.; Chow, E. K. F.; Williams, I. D.; Deng, S.-M. J. Chem. Soc., Dalton Trans. 1996, 1229.
21. Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
22. Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
23. (a) Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570.
24. (b) Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773.
25. Iodocyclization of the corresponding E-isomer under the established conditions proceeded with poor enatioselectivity and moderate chemical conversion (11% ee and 50% yield).
26. (a) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086.
27. (b) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
28. (c) Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773.
29. To investigate the possible involvement of HCl in the cyclization, which might be generated in situ, iodocyclization of 6 was carried out using 0.15 equiv of NCS and 0.6 equiv of HCl instead of 0.75 equiv of NCS to provide (R)-7 in 81% ee and 39% yield.
30. The preparation method of (R,R)-salen-Co(111)Cl was gratefully provided by Mr. Sang Kyun Kim from Prof. Jacobsen's group at Harvard University. Hong, J. Ph.D. Thesis, Harvard University, Cambridge, Massachusetts, 2001.
31. (a) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687.
32. (b) Palucki. M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen. E. N. J. Am. Chem. Soc. 1998, 120, 948.
33. Iodocyclization of 6 was scaled up to 2.6 mmol with comparable enantioselectivity and chemical yield (85% ee and 89% yield).