Enantioselective Construction of Spirooxindole-Fused Cyclopentanes
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
34283607
DOI
10.1021/acs.joc.1c01116
Knihovny.cz E-zdroje
- MeSH
- aldehydy MeSH
- cyklopentany * MeSH
- katalýza MeSH
- spirosloučeniny * MeSH
- stereoizomerie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- aldehydy MeSH
- cyklopentany * MeSH
- spirosloučeniny * MeSH
The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.
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