Reductive Ti-crossed Claisen condensation between methyl α-bromocarboxylates and acid chlorides utilizing a TiCl 4-PPh3-N-methylimidazole reagent

Chemistry Letters

Volumn 36, Issue 1, 2007, Pages 48-49

  Iida, Akira ^a   Nakazawa, Syogo ^a   Nakatsuji, Hidefumi ^a   Misaki, Tomonori ^a   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34247242751     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.48     Document Type: Article

References (26)

1. a) For examples: M. B. Smith, J. March, Advanced Organic Chemistry, 5th ed., Benjamin, New York, 2001, p. 569.
2. b) K. P. C. Vollhardt, N. E. Schore, Organic Chemistry, 3rd ed., Freeman, New York, 1999, p. 1039.
3. c) J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University, New York, 2001, p. 726.
4. d) L. Kürti, B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Burlington, 2005, p. 86 and 138.
5. a) Y. Tanabe, Bull. Chem. Soc. Jpn. 1989, 62, 1917.
6. b) Y. Yoshida, R. Hayashi, H. Sumihara, Y. Tanabe, Tetrahedron Lett. 1997, 38, 8727.
7. c) Y. Yoshida, N. Matsumoto, R. Hamasaki, Y. Tanabe, Tetrahedron Lett. 1999, 40, 4227.
8. d) R. Hamasaki, S. Funakoshi, T. Misaki, Y. Tanabe, Tetrahedron 2000, 56, 7423.
9. e) Y. Tanabe, R. Hamasaki, S. Funakoshi, Chem. Commun. 2001, 1674.
10. f) Y. Tanabe, A. Makita, S. Funakoshi, R. Hamasaki, T. Kawakusu, Adv. Synth. Catal. 2002, 507.
11. g) Y. Tanabe, N. Manta, R. Nagase, T. Misaki, Y. Nishii, M. Sunagawa, A. Sasaki, Adv. Synth. Catal. 2003, 345, 967.
12. a) T. Misaki, R. Nagase, K. Matsumoto, Y. Tanabe, J. Am. Chem. Soc. 2005, 127, 2854.
13. b) A. Iida, S. Nakazawa, T. Okabayashi, A. Horii, T. Misaki, Y. Tanabe, Org. Lett., in press.
14. A. Iida, K. Takai, T. Okabayashi, T. Misaki, Y. Tanabe, Chem. Commun. 2005, 3171.
15. a) Y. Hashimoto, H. Konishi, S. Kikuchi, Synlett 2004, 1264.
16. b) H. Kagoshima, Y. Hashimoto, K. Saigo, Tetrahedron Lett. 1998, 39, 8465.
17. c) Y. Hashimoto, S. Kikuchi, Chem. Lett. 2002, 126.
18. At present, the reason for obtaining of self-condensation product is not so clear.
19. DMAP: a) W. Steglich, G. Hoefle, Angew. Chem., Int. Ed. 1969, 8, 981.
20. b) E. F. V. Scriven, Chem. Soc. Rev. 1983,12, 129.
21. c) A. C. Spivey, S. Arseniyadis, Angew. Chem., Int. Ed. 2004, 43, 5436.
22. W-Methylimidazole: a) A. K. Saha, P. Schultz, H. Rapoport, J. Am. Chem. Soc. 1989, 111, 4856.
23. b) F. S. Gibson, H. Rapoport, J. Org. Chem. 1995, 60, 2615.
24. c) K. Wakasugi, A. Iida, T. Misaki, Y. Nishii, Y. Tanabe, Adv. Synth. Catal. 2003, 345, 1209.
25. d) H. Nakatsuji, J. Morita, T. Misaki, Y. Tanabe, Adv. Synth. Catal. 2006, 348, in press.
26. 2O = 3:1-80:1) to give the desired product.