Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 24, Pages 12668-12675Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02253
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Funding
- NSFC [21372217]
- CAS western light program
- Sichuan Youth Science and Technology Foundation [2013JQ0021, 2015JQ0041]
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Enantioselective Michael/c-ydization cascade reactions of 3-hydroxyoxindoles/3-aminooxindoles with alpha,beta-unsaturated acyl phosphonates by using a cinchonine derived squaramide as the catalyst were developed. A broad range of spirocyclic oxindole-gamma-lactones/lactams could be obtained in moderate to excellent-Yields (up to 98%) with good to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee) under mild conditions. This work represents the first example - about the alpha,beta-unsaturated acyl phosphonates for the asymmetric construction of spirocyclic oxindoles.
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