Synthesis of new enantiomerically pure α,β-unsaturated bicyclic lactams

Tetrahedron Letters

Volumn 44, Issue 41, 2003, Pages 7667-7669

  Agami, Claude ^a   Beauseigneur, Alice ^a   Comesse, Sébastien ^a   Dechoux, Luc ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

2 pyrrolinones; N acyl iminium; Oxazolidines; Unsaturated bicyclic lactams; enaminoesters

Indexed keywords

LACTAM DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0141852849     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.017     Document Type: Article

References (12)

1. For reviews see: (a) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1.
2. For reviews see: (a) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1.
3. Groaning M.D., Brengel G.P., Meyers A.I. Tetrahedron. 57:2001;2635.
4. Groaning M.D., Meyers A.I. Tetrahedron Lett. 40:1999;4639.
5. Fray A.H., Meyers A.I. J. Org. Chem. 61:1996;3362.
6. Kopach M.E., Fray A.H., Meyers A.I. J. Am. Chem. Soc. 118:1996;9876.
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8. Resek J.E., Meyers A.I. Tetrahedron Lett. 36:1995;7051.
9. The stereoselective synthesis of β-enaminocarbonylated compounds has already been described. See: Agami C., Dechoux L., Hebbe S., Moulinas J. Synthesis. 2002;79.
10. Caballero E., Puebla P., Domercq M., Medarde M., Lopez J.L., San Feliciano A. Tetrahedron. 50:1994;7849.
11. A related reaction was recently reported by Amat et al. In their article, the authors present the unprecedented oxidation of a phenylglycinol-derived 2-pyridone, leading to a chiral non-racemic unsaturated hydroxylated bicyclic lactam, which has been used as a precursor in the formal synthesis of the azasugar epiisofagomine. See: Amat M., Llor N., Huguet M., Molins E., Espinosa E., Bosch J. Org. Lett. 3:2001;3257.
12. 3): 21.4, 52.7, 58.1, 76.3, 100.3, 125.8, 127.8, 128.9, 134.3, 139.1, 151.6, 161.6, 174.8.