Cycloadditions of 2-aza-1,3-dienes to aldehydes: A Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives

Tetrahedron Letters

Volumn 40, Issue 39, 1999, Pages 7079-7082

  Ntirampebura, Deogratias ^a   Ghosez, Léon ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

hydroxyamides; 1,3 oxazinones; 2 azadienes; Aldehydes; Diels Alder cycloadditions; Hydroxyalkylations

Indexed keywords

2 AZA 1,3 DIENE; ALDEHYDE; ALKADIENE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DIASTEREOISOMER; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033600702     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01444-6     Document Type: Article

References (11)

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2. 2. Ghosez, L.; Jnoff, E.; Bayard, Ph.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387-3400 and references cited therein.
3. 3. Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115-6118.
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6. 6. Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 52, 5349-5352.
7. 7. For a recent synthesis of perhydrooxazin-4-ones by an hetero Diels-Alder reaction, see: Panunzio, M.; Villa, M.; Missio, A.; Rossi, T.; Seneci, P. Tetrahedron Lett. 1998, 39, 6585-6588.
8. 3: C: 67.44%, H: 7.68%, N: 5.61%. Found: C: 67.24%, H: 7.47%, N: 5.59%.
9. 9. Hydrolysis of 3a: a mixture of 0.5 g (1 equiv.) of 3a in THF and 4 ml of a 3 M solution of HCl in ethanol was allowed to stay at room temperature for 16 h. Evaporation of the solvents gave an oily residue which was purified by flash chromatography on silica gel (AcOEt:cyclohexane 4:1). The crystalline compound 4a was identical with an authentic sample RN: 29478- 52-2.
10. 10. Barluenga, J.; Joglar, J.; Fustero, S.; Gotor, V.; Krüger, C.; Romão, M. J. Chem. Ber. 1985, 118, 3652-3663.
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