Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 3, Pages 2534-2544Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02653
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Funding
- National Key RAMP
- D Program of China [2018YFC0807301-3]
- National NSFC [21871252, 21801024, 21801026, 21901024]
- Material Evidence Identification Center of Ministry of Public Security [2019CSEEKFKT06]
- Chengdu University [2081919035]
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The study introduces a highly diastereo- and enantioselective cyclopropanation reaction of 3-acylcoumarins with 3-halooxindoles catalyzed by an organocatalyst, resulting in compounds bearing three continuous stereocenters with high to excellent selectivities. The importance of the ammonium ylide intermediate in the catalytic process was revealed through HRMS analysis.
A highly diastereo- and enantioselective cyclopropanation reaction of 3-acylcoumarins with 3-halooxindoles catalyzed by an organocatalyst through a [2 + 1] Michael/intramolecular cyclization process was developed. This scenario provides a facile strategy to access spirooxindole-cyclopropa[c]coumarin compounds bearing three continuous stereocenters, including two vicinal quaternary all-carbon stereocenters with high to excellent diastereo- and enantioselectivities. The HRMS study revealed the vital importance of the ammonium ylide intermediate in the catalytic process.
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