Organocatalytic asymmetric [3+2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with 3-alkenyl-5-arylfuran-2(3H)-ones.
Chem Commun (Camb)
; 52(78): 11708-11711, 2016 Sep 22.
Article
em En
| MEDLINE
| ID: mdl-27711301
ABSTRACT
A highly diastereo- and enantioselective [3+2] cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines and 3-alkenyl-5-arylfuran-2(3H)-ones was developed with 1 mol% thiourea-tertiary amine as the catalyst. A series of spiro[pyrrolidin-3,2'-oxindoles] bearing four consecutive stereocenters, including two vicinal spiro-quaternary chiral centers, were efficiently obtained with excellent results (up to >99% yield, >20 1 dr, and >99% ee).
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article