Organocatalytic asymmetric synthesis of dihydrofuran-spirooxindoles from benzylidene malononitriles and dioxindoles

The first organocatalytic enantioselective synthesis of dihydrofuran-spirooxindoles having a linkage at the 2-position of the dihydrofuran motif has been developed. Dioxindoles and benzylidene malononitriles were employed in this method. The desired spirooxindole products were obtained via a Michael...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-07, Vol.17 (27), p.6557-6561
Main Authors: Balha, Megha, Mondal, Buddhadeb, Pan, Subhas Chandra
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Crystallography
Enantiomers
Isomerization
Michael reaction
Synthesis
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Summary:The first organocatalytic enantioselective synthesis of dihydrofuran-spirooxindoles having a linkage at the 2-position of the dihydrofuran motif has been developed. Dioxindoles and benzylidene malononitriles were employed in this method. The desired spirooxindole products were obtained via a Michael reaction followed by a Pinner reaction and isomerization and good to high yields with moderate diastereo and good to high enantioselectivities were observed. The first organocatalytic asymmetric synthesis of dihydrofuran-spirooxindoles having a linkage at the 2-position of the dihydrofuran motif has been developed from dioxindoles and benzylidene malononitriles.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01199d