Catalytic process for efficient enantiodivergence of meso-N,N'-diacetyl- 2-imidazolidinones and DL-N-acetyl-2-oxazolidinones

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6317-6320

  Hashimoto, Noriaki ^a   Ishizuka, Tadao ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLIDINONE; N ACETYL 2 OXAZOLIDINONE; N,N' DIACETYL 2 IMIDAZOLIDINONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DEACYLATION; ENANTIOMER; RACEMIC MIXTURE;

EID: 0032572903     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01340-9     Document Type: Article

References (15)

1. 1. a) Matsunaga, H : Kimura, K. : Ishizuka, T. : Haratake, M. : Kunieda, T. Tetrahedron Lett., 1991, 32, 7715.
2. b) Kimura, K. : Murata, K. : Otsuka, K. : Ishizuka, T. : Haratake, M. : Kunieda, T. Tetrahedron Lett., 1992, 33, 4461.
3. c) Hashimoto, N. : Ishizuka, T. : Kunieda, T. Tetrahedron Lett., 1994, 35, 721.
4. d) Ishizuka, T. : Kunieda, T. J. Syn. Org. Chem. Jpn., 1995, 53, 95.
5. e) Ishizuka, T. : Kunieda, T. Reviews on Heteroatom Chemistry, 1996, 15, 227.
6. 2. Yokoyama, K. : Ishizuka, T. : Kunieda, T. Tetrahedron Lett., 1998, in press.
7. 3. Ishizuka, T. : Kimura, K. : Ishibuchi, S. : Kunieda, T. Chem. Lett., 1992, 991.
8. 4. Hashimoto, N. : Ishizuka, T. : Kunieda, T. Heterocycles, 1997, 46, 189.
9. 3).
10. 3).
11. 7. Corey, E. J. : Bakshi, R. K. : Shibata, S. : J. Am. Chem. Soc. 1987, 109, 555.
12. 2 (0.1 mmol) in THF (2 ml) was stirred at room temperature for 15 min. and 10b (0.5 mmol) was then added at 0 °C. To the mixture, a 0.4 M solution of thexylborane (1 mmol) in THF was added dropwise, followed by stirring at room temperature for 8 h. The work-up, as above, gave an 81% yield of 11b in 98% ee.
13. 3) δ : 5.86 (1H, brs), 4.63 (1H, d, J=8.5 Hz), 3.75 (1H, d, J=8.5 Hz), 2.42 (3H, s), 1.58 (3H, s), 1.49 (3H, s), 1.03 (3H, s), 0.73 (3H, s), 0.63 (3H, s). The absolute configuration is tentatively assigned, based on comparison with 11a and b.
14. 3) δ : 7.32 (8H, m), 4.62 (1H, d, J=8.4 Hz), 4.49 (1H, d, J=8.4 Hz), 2.41 (3H, s), 2.09 (3H, s), 1.93 (3H, s).
15. 3) δ : 7.32 (8H, m), 5.05 (1H, d, J=3.5 Hz), 4.78 (1H, dd, J=3.5, 8.5 Hz), 4.68 (1H, d, J=3.5 Hz), 4.55 (1H, dd, J=3.5, 8.5 Hz), 2.32 (3H, s).