Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2145-2148

  Arai, Shigeru ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CINCHONINE; PHENACYL CHLORIDE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; POLYMERIZATION;

EID: 0032499049     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00081-1     Document Type: Article

References (34)

1. 1. Noyori, R. Asymmetric Catalysis In Organic Synthesis; John Wiley and Sons: New York, 1994.
2. 2. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993
3. 3. For recent books on PTC, see (a) Phase-Transfer Catalysis. Mechanism and Syntheses; Halpern, M. E., Ed.; American Chemical Society, Washington, D C, 1997.
4. (b) Handbook of Phase Transfer Catalysis; Sasson, Y; Neumann, R. Ed.; Blackie A. & M., London, 1997.
5. 4. Fedorynski, M.; Wojciechowski, K.; Matacz, Z.; Makosza, M. J. Org. Chem. 1978, 43, 4682-4684.
6. 5. Diez-Barra, E.; Hoz, A.; Merino, S.; Sanchez-Verdu, P. Tetrahedron Lett. 1997. 38, 2359-2362.
7. 6. (a) Sato, K.; Aoki, M. Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310-8311.
8. (b) Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M. J. Org. Chem. 1988, 53, 3587-3593.
9. (c) Venturello, C.; DAlosio, R. J. Org. Chem. 1988, 53, 1553-1557.
10. 7. Colonna, S.; Fornasier, R. J. Chem. Soc. Perkin I. 1978, 371-373.
11. 8. Cram. D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625-628.
12. 9. Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu. L. E. J. Chem. Soc. Chem. Commun. 1997. 739-740. and references cited therein.
13. 10. (a) O'Donnell, M. J.; Bennett, W.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355.
14. (b) O'Donnell, M.; W.; Wu, S. Tetrahedron Asymmetry, 1992, 3, 591-594.
15. (c) Lipkowtz, K. B.; Cavanaugh, M. W.; Baker, B.; O'Donnell, M. J. J. Org. Chem. 1991, 56, 5181-5192.
16. (d) Dolling, U. -H.; Davis, P.; Grabowski, E. J. Am. Chem. Soc. 1984, 106, 446-447.
17. (e) Hughles, D. L.; Dolling, U. -H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745-4752.
18. (f) Masui, M. Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835-2838.
19. 11. (a) Hummelen, J. C.; Wynberg, H. Tetrahedron Lett. 1978, 1089-1092.
20. (b) Colonna, S.; Fornasier, R.; Pfeiffer, U. J. Chem. Soc. Perkin Trans, I, 1978. 8-11.
21. (c) Annunziata, R.; Banfi, S.; Clonna, S. Tetrahedron Lett. 1985, 26, 2471-2474.
22. (d) Masaki, Y.; Shi, M. J. Chem. Research (S), 1995, 40-41.
23. Recently chiral crown ether catalyzed asymmetric Darzens condensation was reported: (e) Bako. P.; Szollosy, A.; Toke, L. Synlett, 1997. 291-292.
24. 12. Ohkata, K.; Kimura, J.; Shinohara, Y.; Takagi, R.; Hiraga, Y. J. Chem. Soc. Chem. Commun. 1996. 2411-2412.
25. 13. The chiral ammonium hydroxide is difficult to generate because the equilibrium dramatically shifts to the ammonium halide. See : ref. 3 (b) Chapter 4.
26. 14. PTC A was purchased from Aldrich Chemical Co., Ltd.
27. 2 were not effective in this reaction system.
28. 16. The epoxyketone 3a was obtained with a lower ee using other ether solvents such as THF, diethyl ether, diisopropyl ether, t-butyl methyl ether, and 1,4-dioxane.
29. 17. In the case of the use of LiOH as a base, the reaction rate was much slower in the presence or absence of PTC than the use of NaOH or KOH in any solvents.
30. 2 : 3% ee).
31. 3). Enantiomeric excess was determined by HPLC analysis using DAICEL CHIRALCEL OD, hexane:i-PrOH = 50:1. The retention time was 8.3 min for the (αS,βR)-isomer and 9.9 min for the (αR,βS)-isomer.
32. 20. As to the asymmetric synthesis of α,β-epoxyketones, the excellent results by use of catalytic epoxidation of α,β-unsaturated ketones were reported: (a) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc., 1997, 119, 2329-2330.
33. (b) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murry, P. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 410-412.
34. 21. Enders, D.; Zhu, J.; Raabe, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1725-1728.