Solid-phase synthesis of dihydropyrans by Eu(fod)3-catalysed [4+2] heterocycloaddition of vinyl ethers with benzylidenepyruvic acid esters. Comparison with conventional homogeneous liquid phase conditions

European Journal of Organic Chemistry

Volumn , Issue 4, 2000, Pages 639-643

  Leconte, Stéphane ^a   Dujardin, Gilles ^a   Brown, Eric ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

Dihydropyrans; Hetero Diels Alder reactions; Reductive cleavage; Solid phase synthesis; Wang resin

Indexed keywords

BENZYLIDENE DERIVATIVE; BENZYLIDENEPYRUVIC ACID; DIHYDROPYRIDINE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ESTERIFICATION; REACTION ANALYSIS; REDUCTION; SOLID PHASE EXTRACTION; STEREOCHEMISTRY;

EID: 0034006819     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200002)2000:4<639::AID-EJOC639>3.0.CO;2-6     Document Type: Article

References (9)

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4. The Wang resin (Lancaster) contained from 0.8 to 1.1 mmol of OH groups per gram. We used the latter value when calculating the overall yields of the syntheses of endolexo-5a-h.
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8. 4 has only been reported for reductive cleavage of supported amides and carbamates into amines. See for instance: C. Y. Ho, M. J. Kukla, Tetrahedron Lett. 1997, 38, 2799-2302.
9. D. L. Boger, K. D. Robarge, J. Org. Chem. 1988, 53, 3373-3377.