Amino acid derived phosphine-catalyzed enantioselective 1,4-dipolar spiroannulation of cyclobutenones and isatylidenemalononitrile.
Chemistry
; 21(11): 4224-8, 2015 Mar 09.
Article
em En
| MEDLINE
| ID: mdl-25630968
ABSTRACT
Cyclobutenones have been explored as a new type of chiral 1,4-dipole four-carbon synthon, which readily undergoes organophosphine-mediated C-C bond cleavage and asymmetric intermolecular 1,4-dipolar spiroannulation with isatylidenemalononitrile in the presence of amino acid-derived chiral phosphine catalyst to furnish enantioenriched 3-spirocyclohexenone 2-oxindoles in good yield with up to 87%â
ee. To our knowledge, this is the first example of asymmetric transformation of cyclobutenones and the phosphine-catalyzed asymmetric 1,4-dipolar cycloaddition consisting of C-C bond activation is unprecedented.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Fosfinas
/
Ciclobutanos
/
Aminoácidos
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article