On the configuration of (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Tetrahedron Asymmetry

Volumn 14, Issue 3, 2003, Pages 293-295

  Amat, Mercedes ^a   Llor, Núria ^a   Escolano, Carmen ^a   Huguet, Marta ^a   Pérez, Maria ^a   Molins, Elies ^b   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5 OXO 3 PHENYL 2,3,6,7,8,8A HEXAHYDRO 5H OXAZOLO[3,2 A]PYRIDINE; LACTAM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CIS TRANS ISOMERISM; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0037423124     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00837-6     Document Type: Article

References (19)

1. Amat M., Llor N., Bosch J. Tetrahedron Lett. 35:1994;2223-2226.
2. Amat M., Bosch J., Hidalgo J., Cantó M., Pérez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074-3084.
3. Royer J., Husson H.-P. Heterocycles. 36:1993;1493-1496.
4. Micouin L., Quirion J.-C., Husson H.-P. Synth. Commun. 26:1996;1605-1611.
5. Amat M., Pshenichnyi G., Bosch J., Molins E., Miravitlles C. Tetrahedron: Asymmetry. 7:1996;3091-3094.
6. Terán J.L., Gnecco D., Galindo A., Juárez J., Bernès S., Enríquez R.G. Tetrahedron: Asymmetry. 12:2001;357-360.
7. A similar result was observed when using 3N MeOH-HCl.
8. For the preparation of ent-1 and ent-2 from (S)-phenylglycinol following this procedure, see Ref. 4.
9. Amat M., Llor N., Huguet M., Molins E., Espinosa E., Bosch J. Org. Lett. 3:2001;3257-3260.
10. Amat M., Llor N., Hidalgo J., Bosch J., Molins E., Miravitlles C. Tetrahedron: Asymmetry. 7:1996;2501-2504.
11. -3.
12. Rodríguez R., Estiarte M.A., Diez A., Rubiralta M., Colell A., García-Ruiz C., Fernández-Checa J.C. Tetrahedron. 52:1996;7727-7736.
13. Amat M., Pérez M., Llor N., Bosch J., Lago E., Molins E. Org. Lett. 3:2001;611-614.
14. Amat M., Pérez M., Llor N., Bosch J. Org. Lett. 4:2002;2787-2790.
15. Amat M., Cantó M., Llor N., Escolano C., Molins E., Espinosa E., Bosch J. J. Org. Chem. 67:2002;5343-5351 See also Refs. 1b, 4, 8, and 9.
16. For reviews on chiral, amino alcohol-derived bicyclic lactams, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8; (c) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
17. For reviews on chiral, amino alcohol-derived bicyclic lactams, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8; (c) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
18. For reviews on chiral, amino alcohol-derived bicyclic lactams, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8; (c) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
19. 1H NMR data taken from Ref. 1b. Lactam 1: δ 4.01 (dd, J=9.0 and 1.5 Hz, 1H, H-2), δ 4.15 (dd, J=9.0 and 7.0 Hz, 1H, H-2), δ 4.92 (dd, J=7.0 and 1.5 Hz, 1H, H-3). Lactam 2: δ 3.76 (dd, J=9.0 and 8.0 Hz, 1H, H-2), δ 4.50 (dd, J=9.0 and 8.0 Hz, 1H, H-2), δ 5.28 (t, J=8.0 Hz, 1H, H-3).