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The organocatalytic asymmetric Neber reaction for the enantioselective synthesis of spirooxindole 2H-azirines
- Source :
- Organic & Biomolecular Chemistry. 14:10946-10952
- Publication Year :
- 2016
- Publisher :
- Royal Society of Chemistry (RSC), 2016.
-
Abstract
- The asymmetric Neber reaction of 3-O-sulfonyl ketoxime, in situ generated from isatin ketoxime and sulfonyl chloride, for the synthesis of chiral spirocyclic oxindole compounds is reported. With the developed protocol, a range of chiral spirooxindole 2H-azirines could be obtained in good to excellent yields and up to a 92 : 8 enantiomeric ratio by using (DHQD)2PHAL as the catalyst. This methodology is the only example of the catalytic asymmetric construction of spirooxindole 2H-azirine compounds.
- Subjects :
- Azirines
010405 organic chemistry
Isatin
Organic Chemistry
Enantioselective synthesis
Stereoisomerism
Chemistry Techniques, Synthetic
010402 general chemistry
01 natural sciences
Biochemistry
Sulfonyl chloride
Catalysis
0104 chemical sciences
chemistry.chemical_compound
chemistry
Organic chemistry
Spiro Compounds
Oxindole
Physical and Theoretical Chemistry
Enantiomer
Subjects
Details
- ISSN :
- 14770539 and 14770520
- Volume :
- 14
- Database :
- OpenAIRE
- Journal :
- Organic & Biomolecular Chemistry
- Accession number :
- edsair.doi.dedup.....5a4e0d284e07bb3e9ec7f09f4585b4fb