Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 17, Pages 4823-4832Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700227
Keywords
acetylides; allenolates; cycloaddition; organocatalysis; water chemistry
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A study of the reactivity pattern associated with zwitterionic allenolates on water is reported. This study establishes the chemical basis for two organocatalyzed allenolate-driven reaction networks operating on water. The first one is a chemodifferentiating three building block (ABB') three-component reaction (ABB' 3CR) manifold comprising terminal alkynoates and aldehydes. The manifold produces propargylic enol ethers 3 with higher average efficiency than their homologues in organic solvents. The second one is a novel organocatalytic system elicited by the reaction of alkynoates and nitrones in the presence of tertiary amines or phosphines. While terminal alkynoates afford 2,3,5-trisubstituted 2,3-dihydroisoxazoles 5 and propargylic N-hydroxylamines 6, internal alkynoates selectively afford the 2,3,4,5-tetrasusbstituted 2,3-dihydroisoxazaole 10. Importantly, in both cases, the 2,3-dihydroisoxazole ring is obtained as a sole regioisomer.
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