Synthesis, reaction, and structure of chiral N-methyl-2-oxazolidinones from 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8219-8222

  Kawano, Tomikazu ^a   Negoro, Kenji ^a   Ueda, Ikuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 ETHOXY 6 (N TERT BUTOXYCARBONYL)AMINO 2,4 HEXADIENOIC ACID; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL TRANSFORMATION; CHIRALITY; CRYSTAL STRUCTURE; DRUG SYNTHESIS; NONHUMAN; POLYMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0030722020     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10199-X     Document Type: Article

References (14)

1. (a) Evans, D. A. in "Asymmetric Synthesis" Morrison, J. D. Ed.; Academic Press: London, 1984; Vol. 3, pp. 87-90.
2. (b) Heathcock, C. H. Ibid., pp. 184-188.
3. Kunz, H.; Waldman, H. in "Comprehensive Organic Synthesis" Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991, Vol. 6, pp. 635-648.
4. Tanaka, Y.; Kawano, T.; Islam, S. Md.; Nishioka, H.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull. 1996, 44, 885-891.
5. Kawano, T.; Islam, S. Md.; Jeong, J. -S.; Ueda, I. Chem. Lett. 1997, 737-738.
6. Kawano, T.; Ogawa, T.; Islam, S. Md.; Ueda, I. Tetrahedron Lett. 1995, 36, 7665-7688.
7. Huet, F.; Lechevallier, A.; Pellet, M.; Conia, M. Synthesis, 1978, 63-65.
8. Fehrentz, J. -A.; Castro, B. Synthesis, 1983, 676-678.
9. Hatanaka, M.; Himeda, Y.; Imashiro, R.; Tanaka, Y.; Ueda, I. J. Org. Chem. 1994, 59, 111-119.
10. 3). As 4 are converted gradually to an N-methylpyrrole ring at room temperature, storage of the compounds should be done with care, keeping the temperature below -30°C.
11. w were 0.058 and 0.060 for 1378 observed reflections (I>3.00 (σ) I). The structure was solved by direct method (SAPI91) and refined by full-matrix least-squares techniques. Diffraction data were obtained using Rigaku AFC5R diffractometer at -75 °C.
12. Further studies on the formation of pyrrole ring are in progress.
13. Agami, C.: Couty, F.; Haman, L.; Venier, O. Tetrahedron.Lett. 1993, 34, 4509-4512.
14. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232