TiCl4/Bu3N/(catalytic TMSOTf): Efficient agent for direct aldol addition and claisen condensation

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8727-8730

  Yoshida, Yoshihiro ^a   Hayashi, Ryosuke ^a   Sumihara, Hiromasa ^a   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OXOACID;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030782489     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10320-3     Document Type: Article

References (35)

1. a) Mukaiyama, T. Organic Reactions; Wiley: New York, 1982; Vol. 28, p. 203.
2. b) Heathcock, C. H. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming I. Eds.; Pergamon: Oxford, 1991; Vol. 2, p. 181.
3. Heathcock, C. H. In Asymmetric Synthesis, Morrison, J. D., Ed.; Academic Press: New York, 1984, p. 111.
4. Masamune, S.; Choy, W.; Peterson, J. S.; Rita, L. R. Angew. Chem. Int. Ed Engl. 1985, 24, 1.
5. a) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866.
6. b) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
7. Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 112, 1047.
8. Harrison, C. R. Tetrahedron Lett. 1987, 28, 4135.
9. e) Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. Tetrahedron 1991, 47, 7897.
10. f) Xiang, Y. Olivier, E.; Ouimet, N. Tetrahedron Lett. 1992, 33, 457.
11. g) Yan, T-H.; Lee, H-C.; Tan, C-W. Tetrahedron Lett. 1993, 34, 3559.
12. 3N or TMEDA was reported
13. Mahrwald, R.; Costisella, B.; Gundogan, B. Tetrahedron Lett. 1997, 38, 4543.
14. Mukaiyama, T.; Iwasawa, N.; Stevens, R. W.; Haga, T. Tetrahedron 1984, 40, 1381.
15. 4/amine was reported.
16. b) Lehnert, W. Tetrahedron Lett. 1970, 4723.
17. Brocchini, S. J. Eberle, M. Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. It is reported that the oxidative coupling of phenylacetic acid esters competes with self-Claisen condensation of them.
18. Matsumura, Y.; Nishimura, M.; Hiu, H.; Watanabe, M.; Kise, N. J. Org. Chem. 1996, 61, 2809. For other recent useful Claisen-type (the Dieckmann) condensation:
19. e) Nagao, Y.; Hagiwara, Y.; Tohjo, T.; Hasegawa, Y.; Ochiai, M.; Shiro, M. J. Org. Chem. 1988, 53, 5983.
20. f) Tamai S.; Ushirogochi, H.; Sano, S.; Nagao, Y. Chem. Lett. 1995, 295.
21. g) Sano, S.; Ushirogochi, H.; Morimoto, K.; Tamai, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1996, 1775.
22. h) Sibi, M. P.; Christensen, J. W.; Kim, S-G.; Eggen, M. Tetrahedron Lett. 1995, 36, 6209.
23. h) Oppolzer, W.; Rodriguez, I. Helv. Chem. Acta 1993, 76, 1275.
24. 3
25. This direct cross coupling between different aliphatic ketones may be the first example.
26. We presently speculate that Ti(IV) forms more a rigid 6-membered chair transition state leading to the syn-aldol compared with Sn(II) due to the strong Lewis acidity of Ti(IV). Stereochemical considerations of the titanium enolates with aldehydes is extensively studied a) Refs. 2a and 2c.
27. b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343.
28. 2 column chromatography (hexane-AcOEt = 12:1) gave methyl 2-benzyl-4-chloro-3-oxopentanoate (185 mg, 73 %).
29. 2NEt (78%), and N-ethylpiperidine (69%).
30. Titanium triflates are used for useful acylation-type reactions: a) Izumi, J.; Shiina, I.; Mukaiyama, T. Chem. Lett. 1995, 141.
31. b) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267.
32. Tanabe, Y.; Mukaiyama, T. Chem. Lett. 1985, 673.
33. Tanabe, Y. Bull. Chem. Soc. Jpn. 1994, 67, 3309.
34. 3N reagent are reported. a) Yamaguchi M.; Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362.
35. b) Yamaguchi M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479.