Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 7, Pages 1490-1495Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000001
Keywords
dipeptide-based phosphonium salt; phase transfer catalysis; 3,2 '-pyrrolidinyl spirooxindole; asymmetric synthesis; 1,3-dipolar cyclization
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Funding
- National Key R&D Program of China [2018YFA0903500]
- National Natural Science Foundation of China [21702139, 21971165, 21921002]
- Fundamental Research Funds for the Central Universities
- 1000-Youth Talents Program [YJ201702]
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Reported here is an alternative method for asymmetric synthesis of the CF3-substituted 3,2 '-pyrrolidinyl spirooxindoles via 1,3-dipolar cycloaddition by employing dipeptide-based chiral phosphonium salt as a phase-transfer catalyst. Under the optimal reaction conditions, a variety of CF3-substituted 3,2 '-pyrrolidinyl spirooxindole derivatives were readily prepared in high yields as a single diastereomer with high enantiomeric access (>20:1 dr and up to 94% ee).
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