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Dual reactivity pattern of allenolates "on water": the chemical basis for efficient allenolate-driven organocatalytic systems

AuthorsGonzález-Cruz, David ; Tejedor, David ; Armas, Pedro de ; García-Tellado, Fernando
Water chemistry
Issue Date20-Apr-2007
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 13(17): 4823-4832 (2007)
AbstractA 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.
Description10 pages, 4 tables, 7 schemes.-- PMID: 17450516 [PubMed].-- Printed version published Jun 4, 2007.
Publisher version (URL)http://dx.doi.org/10.1002/chem.200700227
Appears in Collections:(IPNA) Artículos
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