Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 46, Pages 10946-10952Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob02220k
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Funding
- National Natural Science Foundation of China [21372217, 21572223, 21572224]
- Sichuan Youth Science and Technology Foundation [2013JQ0021, 2015JQ0041, 2016JQ0021]
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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)(2)PHAL as the catalyst. This methodology is the only example of the catalytic asymmetric construction of spirooxindole 2H-azirine compounds.
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