Solid-phase domino syntheses of functionalized tetronates with Ph3P=C=C=O

Tetrahedron Letters

Volumn 44, Issue 34, 2003, Pages 6449-6451

  Schobert, Rainer ^a   Jagusch, Carsten ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

POLYSTYRENE; TETRONIC ACID DERIVATIVE;

ARTICLE; HORNER REACTION; IMMOBILIZATION; SOLID; SYNTHESIS;

EID: 0041696579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01582-X     Document Type: Article

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12. -1 (C=O).
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19. General procedure for the benzylation of tetronic acids to give 6: 5 (1.25 mmol) was suspended in THF (5 mL) and O-benzyl-N,N′-dicyclohexylisourea (0.5 g, 1.3 equiv.) was added. The mixture was shaken for 16 h at 50-60°C. The resin was washed thoroughly with DMF (2×10 mL), THF (2×10 mL), MeOH (2×10 mL) and DCM (2×10 mL) and dried in vacuo.
20. Cleavage of 6 to give 7: Benzyl tetronate 6 (1.25 mmol) was swollen in DCM (5 mL) for 30 min and finally filtered. 10 mL of the cleavage solution (TFA/DCM 9:1) and 5% triisopropylsilane (0.5 mL) were added and the mixture was shaken for 4 h at rt. The resin was filtered and washed twice with 5 mL of DCM. The filtrate was evaporated to dryness. Quantitative conversion was found by weighing the crude and the identity of the products was determined by ESI-MS, NMR and IR.