Issue 46, 2016

The organocatalytic asymmetric Neber reaction for the enantioselective synthesis of spirooxindole 2H-azirines

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.

Graphical abstract: The organocatalytic asymmetric Neber reaction for the enantioselective synthesis of spirooxindole 2H-azirines

Supplementary files

Article information

Article type
Paper
Submitted
12 Oct 2016
Accepted
01 Nov 2016
First published
01 Nov 2016

Org. Biomol. Chem., 2016,14, 10946-10952

The organocatalytic asymmetric Neber reaction for the enantioselective synthesis of spirooxindole 2H-azirines

J. Zhao, D. Yue, X. Zhang, X. Xu and W. Yuan, Org. Biomol. Chem., 2016, 14, 10946 DOI: 10.1039/C6OB02220K

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