Highly stereoselective synthesis of trisubstituted cis-[3]cumulenols from alkynylated oxatitanacycles in the presence of Lewis Acids

Organometallics

Volumn 29, Issue 2, 2010, Pages 505-508

  Chen, Jingjin ^a   Liu, Yuanhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; STEREOSELECTIVE METHOD; STEREOSELECTIVE SYNTHESIS;

ACIDS; ALDEHYDES; KETONES; TITANIUM;

STEREOSELECTIVITY;

EID: 74549175876     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900941y     Document Type: Article

References (47)

1. (a) Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68.
2. (b) Myers, A. G.; Cohen, S. B.; Kwon, B. -M. J. Am. Chem. Soc. 1994, 116, 1670.
3. (c) Wang, K. K.; Liu, B.; Lu, Y. J. Org. Chem. 1995, 60, 1885 and the references therein.
4. (a) Skibar, W.; Kopacka, H.; Wurst, K.; Salzmann, C.; Ongania, K.; de Biani, F. F.; Zanello, P.; Bildstein, B. Organometallics 2004, 23, 1024.
5. (b) Bildstein, B. Coord. Chem. Rev. 2000, 206-207, 369.
6. (c) Kinoshita, I.; Kijima, M.; Shirakawa, H. Macromol. Rapid Commun. 2000, 21, 1205.
7. (d) Kijima, M.; Kinoshita, I.; Shirakawa, H. Synth. Met. 1999, 101, 145.
8. (a) Iyoda, M.; Tanaka, S.; Otani, H.; Nose, M.; Oda, M. J. Am. Chem. Soc. 1988, 110, 8494.
9. (b) Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101.
10. (c) Furuta, T.; Asakawa, T.; Iinuma, M.; Fujii, S.; Tanaka, K.; Kan, T. Chem. Commun. 2006, 3648.
11. (d) Guan, X.; Shi, M. J. Org. Chem. 2009, 74, 1977.
12. (a) Hopf, H. In The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Interscience/Wiley: Chichester, 1980; Part 2, Chapter 20, p 781.
13. (b) Brandsma, L.; Verkruijsse, H. D. In Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: New York, 1981.
14. (c) Cao, X. -P.; Leung, M. -K. J. Chem. Soc., Perkin Trans. 1 1995, 193.
15. (d) Chow, H. -F.; Cao, X. -P.; Leung, M. -K. J. Chem. Soc., Chem. Commun. 1994, 2121 and the references cited therein.
16. For stereoselective synthesis of disubstituted [3]cumulenes, see: (a) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604.
17. (b) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Johar, P. S. Bull. Chem. Soc. Jpn. 1993, 66, 9870
18. (c) Ohmura, T.; Yorozuya, S.; Yamamoto, Y.; Miyaura, N. Organametallics 2000, 19, 365.
19. (d) van den Hoek, W. G. M.; Kroon, J.; Kleijn, H.; Westmijze, H.; Vermeer, P.; Bos, H. J. T. J. Chem. Soc., Perkin II 1979, 4231.
20. (e) Yoshida, T.; Williams, R. M.; Negishi, E. J. Chem. Chem. Soc. 1974, 96, 3688.
21. (f) Negishi, E.; Yoshida, T.; Abramovitch, A.; Lew, G.; Williams, R. M. Tetrahedron 1991, 47, 343.
22. 2-promoted non-stereoselective synthesis of [3]cumulenols, see:
23. (b) Aurrecoechea, J. M.; Pérez, E.; Solay, M. J. Org. Chem. 2001, 66, 564.
24. (a) Fu, X.; Chen, J.; Li, G.; Liu, Y. Angew. Chem., Int. Ed. 2009, 48, 5500.
25. (b) Zhou, Y.; Chen, J.; Zhao, C.; Wang, E.; Liu, Y.; Li, Y. J. Org. Chem. 2009, 74, 5326.
26. (c) Chen, J.; Liu, Y. Tetrahedron Lett. 2008, 49, 6655.
27. (d) Song, Z.; Li, Y.; Liu, M.; Cong, L; Liu, Y. Organometallics 2006, 25, 5035.
28. (e) Liu, Y.; Gao, H. Org. Lett. 2006, 8, 309.
29. (f) Liu, Y.; Yan, B. Organometallics 2006, 25, 544.
30. (g) Liu, Y.; Gao, H.; Zhou, S. Angew. Chem., Int. Ed. 2006, 45, 4163.
31. (h) Liu, Y.; Liu, M.; Song, Z. J. Am. Chem. Soc. 2005, 127, 3662.
32. (i) Zhou, S.; Yan, B.; Liu, Y. J. Org. Chem. 2005, 70, 4006.
33. (j) Liu, Y.; Song, F.; Cong, L. J. Org. Chem. 2005, 70, 6999.
34. (k) Zhou, S.; Liu, D.; Liu, Y. Organometallics 2004, 23, 5900.
35. For Lewis acid-promoted reactions of zirconacycles, see: (a) Xi, Z.; Li, P. Angew. Chem., Int. Ed. 2000, 39, 2950.
36. (b) Zhao, C.; Li, P.; Cao, X.; Xi, Z. Chem.-Eur. J 2002, 8, 4292.
37. (c) Zhao, C.; Yu, T.; Xi, Z. Chem. Commun. 2002, 142.
38. (d) Zhao, C.; Yan, J.; Xi, Z. J. Org. Chem. 2003, 68, 4355.
39. (e) Zhao, C.; Lu, J.; Yan, J.; Xi, Z. Tetrahedron Lett. 2003, 44, 6895.
40. (f) Zhao, C.; Lu, J.; Li, Z.; Xi, Z. Tetrahedron 2004, 60, 1417.
41. (g) Lu, J.; Mao, G.; Zhang, W; Xi, Z. Chem. Commun. 2005, 4848.
42. 2 resulted in no formation of cumulenols.
43. 1H NMR in most cases.
44. See Supporting Information.
45. Several trans-[3]cumulenols have been prepared by this method; see Supporting Information.
46. 2, see: Dzhemilev, U. M.; Ibragimov, A. G.; Khafizova, L. O.; Rusakov, S. V.; Khalilov, L. M. Mendeleev Commun. 1997, 7, 198.
47. 2O induced 1,3-isomerization of α-(alkoxy)allyl stannanes, see: Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647.