6533b7dcfe1ef96bd1271e17
RESEARCH PRODUCT
A comparative study of the multicomponent Ugi reactions of an oxabicycloheptene-based β-amino acid in water and in methanol
Reijo SillanpääIván KanizsaiFerenc FülöpZsolt Szakonyisubject
chemistry.chemical_classificationchemistry.chemical_compoundAqueous solutionChemistryOrganic ChemistryDrug DiscoveryOrganic chemistryMethanolBiochemistryAmino aciddescription
Di-exo-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid 1, five aldehydes and two isocyanides were reacted both in methanol and in water to prepare a 10-membered β-lactam library via a Ugi-4-centre-3-component reaction. The yields were found to be similar in water and methanol. The diastereoselectivities of the aqueous reactions were similar, though in a few cases higher than those in methanol. The benefits of water are the facile isolation of the precipitated product and the shorter reaction time.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-12-01 | Tetrahedron Letters |