2024-03-28T19:00:25Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/132382019-11-12T14:22:14Zcom_10261_48com_10261_5col_10261_301
2009-05-26T13:32:48Z
urn:hdl:10261/13238
Dual reactivity pattern of allenolates "on water": the chemical basis for efficient allenolate-driven organocatalytic systems
González-Cruz, David
Tejedor, David
Armas, Pedro de
García-Tellado, Fernando
Ministerio de Educación y Ciencia (España)
Consejo Superior de Investigaciones Científicas (España)
Acetylides
Allenolates
Cycloaddition
Organocatalysis
Water chemistry
10 pages, 4 tables, 7 schemes.-- PMID: 17450516 [PubMed].-- Printed version published Jun 4, 2007.
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.
2009-05-26T13:32:48Z
2009-05-26T13:32:48Z
2007-04-20
artículo
Chemistry - A European Journal 13(17): 4823-4832 (2007)
0947-6539
http://hdl.handle.net/10261/13238
10.1002/chem.200700227
http://dx.doi.org/10.13039/501100003339
eng
http://dx.doi.org/10.1002/chem.200700227
closedAccess
John Wiley & Sons