Aza-Reformatsky-type reaction of α-iodomethyl ketone O-alkyl oximes promoted by titanium tetraiodide

Organic and Biomolecular Chemistry

Volumn 2, Issue 20, 2004, Pages 2891-2892

  Shimizu, Makoto ^a   Toyoda, Tadahiro ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; DERIVATIVES; NEGATIVE IONS; REACTION KINETICS; TITANIUM COMPOUNDS;

ALDOL-TYPE REACTIONS; ENOLATES; REFORMATSKY-TYPE REACTION; TITANIUM TETRAIODIDE;

KETONES;

EID: 8344256439     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b411127c     Document Type: Article

References (33)

1. (a) D. E. Bergbreiter, in Asymmetric Synthesis, J. D. Morrison, ed., Academic Press, New York, 1983, vol. 2, part A, pp. 243-273;
2. (b) M. E. Kuehne, in Examines: A Synthesis, Structure, and Reactions, G. A. Cook, ed., Marcel Dekker, New York, 1969, pp. 314-468;
3. (c) P. W. Hickmott, Tetrahedron, 1982, 38, 1975-2050:
4. (d) P. W. Hickmott, Tetrahedron, 1982, 38, 3363-3446;
5. (e) G. Stork, A. Brizzolara, H. Landesman, J. Szmuskovicz and R. Terrell, J. Am. Chem. Soc., 1963, 85, 207:
6. (f) G. Stork and S. R. Dowd, J. Am. Chem. Soc., 1963, 85, 2178;
7. (g) G. Wittig. H. D. Frommeld and P. Suchanek, Angew. Chem., 1963, 78, 978;
8. (h) E. I. Corey and D. Enders, Tetrahedron Lett., 1975, 3:
9. (i) E. J. Corey and D. Enders, Chem. Ber., 1978, 111, 1337;
10. (j) W. G. Kofron and M.-K. Yen, J. Org. Chem., 1976, 41, 439;
11. (k) A. Q. Hussein, A. A. Jarrar and A. S. Madi, Heterocycles, 1989, 29, 1681;
12. (l) S. Shatzmiller and B.-Z. Dolitzki, Liebigs Ann. Chem., 1991, 189;
13. (m) M. Ortiz-Marciales, M. De Jesus, L. Quinones, D. Figueroa, Y. L. Montes, C. Burgos and B. Moctezuma, Tetrahedron, 1999, 55, 12275.
14. For the preparation of α-halogenated imines, see: N. de Kimpe, R. Verhe, L. de Buyck, L. Moens and N. Schamp, Synthesis, 1982, 43; N. de Kimpe, W. de Cock and C. Stevens, Tetrahedron, 1992, 48, 2739.
15. For the preparation of α-halogenated imines, see: N. de Kimpe, R. Verhe, L. de Buyck, L. Moens and N. Schamp, Synthesis, 1982, 43; N. de Kimpe, W. de Cock and C. Stevens, Tetrahedron, 1992, 48, 2739.
16. M. Shimizu, F. Kobayashi and R. Hayakawa, Tetrahedron, 2001, 57, 9591.
17. (a) M. Shimizu, H. Goto and R. Hayakawa, Org. Lett., 2002, 4, 4097;
18. (b) M. Shimizu and T. Sahara, Chem. Lett., 2002, 888;
19. (c) M. Shimizu, Y. Takeuchi and T. Sahara, Chem. Lett., 2001, 1196;
20. (d) M. Shimizu, T. Sahara and R. Hayakawa, Chem. Lett., 2001, 792:
21. (e) R. Hayakawa, H. Makino and M. Shimizu, Chem. Lett., 2001, 756;
22. (f) R. Hayakawa and M. Shimizu, Org. Lett., 2000, 2, 4079;
23. (g) R. Hayakawa, T. Sahara and M. Shimizu, Tetrahedron Lett., 2000, 41, 7939;
24. (h) M. Shimizu, K. Shibuya and R. Hayakawa, Synlett., 2000, 1437;
25. (i) R. Hayakawa and M. Shimizu, Chem. Lett., 2000, 724.
26. 4) (20.3 mg, 88%) as a colorless oil.
27. C. Rener, W. Huayue and Z. Yongmin, J. Chem. Res. (S), 1999, 666; T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 2000, 65, 5066; K. Maeda, H. Shinokubo and K. Oshima, J. Org. Chem., 1998, 63, 4558; M. Z. Liu, Z. W. Guo and Y. Z. Hui, Youji Huaxue, 1997, 17, 319; R. Lin, L. Chen and Y. Zhang, Youji Huaxue, 1990,10,454; H. N. Borah, R. C. Boruah and J. S. Sandhu, J. Chem. Soc., Chem. Commun., 1991, 154; S. Fukuzawa, T. Tsuruta, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans 1, 1987, 1473.
28. C. Rener, W. Huayue and Z. Yongmin, J. Chem. Res. (S), 1999, 666; T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 2000, 65, 5066; K. Maeda, H. Shinokubo and K. Oshima, J. Org. Chem., 1998, 63, 4558; M. Z. Liu, Z. W. Guo and Y. Z. Hui, Youji Huaxue, 1997, 17, 319; R. Lin, L. Chen and Y. Zhang, Youji Huaxue, 1990,10,454; H. N. Borah, R. C. Boruah and J. S. Sandhu, J. Chem. Soc., Chem. Commun., 1991, 154; S. Fukuzawa, T. Tsuruta, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans 1, 1987, 1473.
29. C. Rener, W. Huayue and Z. Yongmin, J. Chem. Res. (S), 1999, 666; T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 2000, 65, 5066; K. Maeda, H. Shinokubo and K. Oshima, J. Org. Chem., 1998, 63, 4558; M. Z. Liu, Z. W. Guo and Y. Z. Hui, Youji Huaxue, 1997, 17, 319; R. Lin, L. Chen and Y. Zhang, Youji Huaxue, 1990,10,454; H. N. Borah, R. C. Boruah and J. S. Sandhu, J. Chem. Soc., Chem. Commun., 1991, 154; S. Fukuzawa, T. Tsuruta, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans 1, 1987, 1473.
30. C. Rener, W. Huayue and Z. Yongmin, J. Chem. Res. (S), 1999, 666; T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 2000, 65, 5066; K. Maeda, H. Shinokubo and K. Oshima, J. Org. Chem., 1998, 63, 4558; M. Z. Liu, Z. W. Guo and Y. Z. Hui, Youji Huaxue, 1997, 17, 319; R. Lin, L. Chen and Y. Zhang, Youji Huaxue, 1990,10,454; H. N. Borah, R. C. Boruah and J. S. Sandhu, J. Chem. Soc., Chem. Commun., 1991, 154; S. Fukuzawa, T. Tsuruta, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans 1, 1987, 1473.
31. C. Rener, W. Huayue and Z. Yongmin, J. Chem. Res. (S), 1999, 666; T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 2000, 65, 5066; K. Maeda, H. Shinokubo and K. Oshima, J. Org. Chem., 1998, 63, 4558; M. Z. Liu, Z. W. Guo and Y. Z. Hui, Youji Huaxue, 1997, 17, 319; R. Lin, L. Chen and Y. Zhang, Youji Huaxue, 1990,10,454; H. N. Borah, R. C. Boruah and J. S. Sandhu, J. Chem. Soc., Chem. Commun., 1991, 154; S. Fukuzawa, T. Tsuruta, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans 1, 1987, 1473.
32. C. Rener, W. Huayue and Z. Yongmin, J. Chem. Res. (S), 1999, 666; T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 2000, 65, 5066; K. Maeda, H. Shinokubo and K. Oshima, J. Org. Chem., 1998, 63, 4558; M. Z. Liu, Z. W. Guo and Y. Z. Hui, Youji Huaxue, 1997, 17, 319; R. Lin, L. Chen and Y. Zhang, Youji Huaxue, 1990,10,454; H. N. Borah, R. C. Boruah and J. S. Sandhu, J. Chem. Soc., Chem. Commun., 1991, 154; S. Fukuzawa, T. Tsuruta, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans 1, 1987, 1473.
33. C. Rener, W. Huayue and Z. Yongmin, J. Chem. Res. (S), 1999, 666; T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 2000, 65, 5066; K. Maeda, H. Shinokubo and K. Oshima, J. Org. Chem., 1998, 63, 4558; M. Z. Liu, Z. W. Guo and Y. Z. Hui, Youji Huaxue, 1997, 17, 319; R. Lin, L. Chen and Y. Zhang, Youji Huaxue, 1990,10,454; H. N. Borah, R. C. Boruah and J. S. Sandhu, J. Chem. Soc., Chem. Commun., 1991, 154; S. Fukuzawa, T. Tsuruta, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans 1, 1987, 1473.