Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines

This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived - -butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocata...

Full description

Saved in:
Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 22; no. 11; p. 2016
Main Authors Rainoldi, Giulia, Faltracco, Matteo, Spatti, Claudia, Silvani, Alessandra, Lesma, Giordano
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 21.11.2017
MDPI
Subjects
azetidines
Carbon
Catalysis
Chemical reactions
cinchona-based catalysts
Imines
Imines - chemistry
Isatin - chemistry
Models, Chemical
Nitriles - chemistry
Organic chemistry
organocatalysis
Spiro compounds
Spiro Compounds - chemistry
spirooxindoles
organocatalysis
spirooxindoles
cinchona-based catalysts
azetidines
Online AccessGet full text

Cover

More Information
Summary:This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived - -butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules22112016