Enantioselective synthesis of cis-2-oxazoline-4-carboxylates by Lewis acid catalyzed formal [3+2] cycloadditions of 5-alkoxyoxazoles with aldehydes

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 869-872

  Suga, Hiroyuki ^a   Ikai, Kosei ^a   Ibata, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLINE 4 CARBOXYLATE; 5 ALKOXYOXAZOLE; ALDEHYDE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONTROLLED STUDY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; NONHUMAN;

EID: 0032546117     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10752-3     Document Type: Article

References (19)

1. 1. For a review of the syntheses of 2-oxazoline-4-carboxylates using isocyanoacetates and conversion to β-hydroxyamino acid: Matsumoto, K.; Moriya, T.; Suzuki, M. J. Synth. Org. Chem. Jpn. 1985, 43, 7664.
2. 2. Hoppe, D.; Schöllkopphf, U.Justus Liebigs Ann. Chem. 1972, 763, 1. Matsumoto, K.; Urabe, Y.; Ozaki, Y.; Iwasaki, T.; Miyoshi, M. Agric. Biol. Chem. 1975, 39, 1869. Matsumoto, K.; Ozaki, Y.; Suzuki, M.; Miyoshi, M. Agric. Biol. Chem. 1976, 40, 2045. Ozaki, Y.; Matsumoto, K.; Miyoshi, M. Agric. Biol. Chem. 1978, 42, 1565.
3. 2. Hoppe, D.; Schöllkopphf, U.Justus Liebigs Ann. Chem. 1972, 763, 1. Matsumoto, K.; Urabe, Y.; Ozaki, Y.; Iwasaki, T.; Miyoshi, M. Agric. Biol. Chem. 1975, 39, 1869. Matsumoto, K.; Ozaki, Y.; Suzuki, M.; Miyoshi, M. Agric. Biol. Chem. 1976, 40, 2045. Ozaki, Y.; Matsumoto, K.; Miyoshi, M. Agric. Biol. Chem. 1978, 42, 1565.
4. 2. Hoppe, D.; Schöllkopphf, U.Justus Liebigs Ann. Chem. 1972, 763, 1. Matsumoto, K.; Urabe, Y.; Ozaki, Y.; Iwasaki, T.; Miyoshi, M. Agric. Biol. Chem. 1975, 39, 1869. Matsumoto, K.; Ozaki, Y.; Suzuki, M.; Miyoshi, M. Agric. Biol. Chem. 1976, 40, 2045. Ozaki, Y.; Matsumoto, K.; Miyoshi, M. Agric. Biol. Chem. 1978, 42, 1565.
5. 2. Hoppe, D.; Schöllkopphf, U.Justus Liebigs Ann. Chem. 1972, 763, 1. Matsumoto, K.; Urabe, Y.; Ozaki, Y.; Iwasaki, T.; Miyoshi, M. Agric. Biol. Chem. 1975, 39, 1869. Matsumoto, K.; Ozaki, Y.; Suzuki, M.; Miyoshi, M. Agric. Biol. Chem. 1976, 40, 2045. Ozaki, Y.; Matsumoto, K.; Miyoshi, M. Agric. Biol. Chem. 1978, 42, 1565.
6. 3. Ito, Y.; Sawamura, M.; Hayashi, T.; J. Am. Chem. Soc. 1986, 108, 6405. Idem. Tetrahedron Lett., 1987, 28, 6215. Ibid. 1988, 29, 239. Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T.; Ibid., 1988, 29, 235. Idem., Tetrahedron 1988, 44, 5253.
7. 3. Ito, Y.; Sawamura, M.; Hayashi, T.; J. Am. Chem. Soc. 1986, 108, 6405. Idem. Tetrahedron Lett., 1987, 28, 6215. Ibid. 1988, 29, 239. Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T.; Ibid., 1988, 29, 235. Idem., Tetrahedron 1988, 44, 5253.
8. 3. Ito, Y.; Sawamura, M.; Hayashi, T.; J. Am. Chem. Soc. 1986, 108, 6405. Idem. Tetrahedron Lett., 1987, 28, 6215. Ibid. 1988, 29, 239. Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T.; Ibid., 1988, 29, 235. Idem., Tetrahedron 1988, 44, 5253.
9. 3. Ito, Y.; Sawamura, M.; Hayashi, T.; J. Am. Chem. Soc. 1986, 108, 6405. Idem. Tetrahedron Lett., 1987, 28, 6215. Ibid. 1988, 29, 239. Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T.; Ibid., 1988, 29, 235. Idem., Tetrahedron 1988, 44, 5253.
10. 3. Ito, Y.; Sawamura, M.; Hayashi, T.; J. Am. Chem. Soc. 1986, 108, 6405. Idem. Tetrahedron Lett., 1987, 28, 6215. Ibid. 1988, 29, 239. Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T.; Ibid., 1988, 29, 235. Idem., Tetrahedron 1988, 44, 5253.
11. 4. Kaneko, T.; Katsura, H. Bull. Chem. Soc. Jpn. 1963, 36, 899. Seebach, D.; Aebi, J. D. Tetrahedron Lett, 1983, 24, 3311. Gou, D.-M.; Lui, Y.-C; Chen, C.-S. J. Org. Chem. 1993, 58, 1287. Kingston, D. G.; Chaudhary, A. G.; Gunatilaka, A. A. L.; Middleton, M. L. Tetrahedron Lett. 1994, 35, 4483.
12. 4. Kaneko, T.; Katsura, H. Bull. Chem. Soc. Jpn. 1963, 36, 899. Seebach, D.; Aebi, J. D. Tetrahedron Lett, 1983, 24, 3311. Gou, D.-M.; Lui, Y.-C; Chen, C.-S. J. Org. Chem. 1993, 58, 1287. Kingston, D. G.; Chaudhary, A. G.; Gunatilaka, A. A. L.; Middleton, M. L. Tetrahedron Lett. 1994, 35, 4483.
13. 4. Kaneko, T.; Katsura, H. Bull. Chem. Soc. Jpn. 1963, 36, 899. Seebach, D.; Aebi, J. D. Tetrahedron Lett, 1983, 24, 3311. Gou, D.-M.; Lui, Y.-C; Chen, C.-S. J. Org. Chem. 1993, 58, 1287. Kingston, D. G.; Chaudhary, A. G.; Gunatilaka, A. A. L.; Middleton, M. L. Tetrahedron Lett. 1994, 35, 4483.
14. 4. Kaneko, T.; Katsura, H. Bull. Chem. Soc. Jpn. 1963, 36, 899. Seebach, D.; Aebi, J. D. Tetrahedron Lett, 1983, 24, 3311. Gou, D.-M.; Lui, Y.-C; Chen, C.-S. J. Org. Chem. 1993, 58, 1287. Kingston, D. G.; Chaudhary, A. G.; Gunatilaka, A. A. L.; Middleton, M. L. Tetrahedron Lett. 1994, 35, 4483.
15. 5. Gold(I)-catalyzed asymmetric aldol reaction of methy isocyanoacetate with penta- and tetrafluorobenzaldehydes showed cis-selectivity (cis:trans = 63:37-62:38) with high enentioselectivity (86% ee - 90% ee): Soloshonok, V. A.; Hayashi, T. Tetrahedron Lett., 1994, 35, 2713.
16. 6. Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397.
17. 7. Suga, H.; Fujieda, H.; Hirotsu, Y.; Ibata, T. J. Org. Chem. 1994, 59, 3359.
18. 3Al : (R)-BINOL = 1 : 1.05), the reaction (5 °C, 45 h) was not completed (61% yield, recovered 1b: 31%) and showed low selectivity (cis : trans = 79 : 21, cis: 63%ee).
19. D = - 50.2 ± 2 ° (c 2.0, 6N HCl): Vogler, K. Helv. Chim. Acta 1950, 33, 2111.). (Equation Presented)