Asymmetric [3 + 2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3'-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters.
J Org Chem
; 83(17): 10465-10475, 2018 09 07.
Article
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| MEDLINE
| ID: mdl-29966096
ABSTRACT
A highly regio- and stereoselective [3 + 2] cycloaddition reaction for constructing novel 3,3'-cyclopentenyldispirooxindoles incorporating two adjacent quaternary spirostereocenters is reported. Under the mild conditions, the asymmetric annulation of isatin-derived MBH carbonates with 3-methyleneoxindoles involving a chiral tertiary amine catalyst provides the corresponding dispirooxindole frameworks with an extraordinary level of enantioselective control. Further synthetic utility of this method was demonstrated by the gram-scale experiment and simple transformation of the obtained product. Moreover, a plausible mechanism for this annulation reaction was also proposed on the basis of the control experiments.
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1
Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2018
Tipo del documento:
Article
País de afiliación:
China