Organocatalyzed Enantioselective [3+2] Cycloaddition Reactions for Synthesis of Dispiro[benzothiophenone-indandione-pyrrolidine] Derivatives

An organocatalytic enantioselective [3+2] cycloaddition reaction involving 2-arylidene-1,3-indandiones and N-2,2-difluoroethylbenzothiophenone imines was developed. This approach efficiently afforded dispiro[benzothiophenone-indandione-pyrrolidine]s, featuring three stereocenters, in 84–98% yields w...

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Published inMolecules (Basel, Switzerland) Vol. 29; no. 20; p. 4856
Main Authors Liu, Hong-Yan, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.10.2024
MDPI
Subjects
2-arylidene-1,3-indandione
asymmetric catalysis
benzothiophenone
Cancer
Chlorine
Clinical medicine
Diffraction
Fluorine
Medical research
Performance evaluation
Solvents
spirocyclic compounds
squaramide
thiourea
X-rays
thiourea
asymmetric catalysis
squaramide
2-arylidene-1,3-indandione
spirocyclic compounds
benzothiophenone
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Summary:An organocatalytic enantioselective [3+2] cycloaddition reaction involving 2-arylidene-1,3-indandiones and N-2,2-difluoroethylbenzothiophenone imines was developed. This approach efficiently afforded dispiro[benzothiophenone-indandione-pyrrolidine]s, featuring three stereocenters, in 84–98% yields with 3–93% ee and 9:1–>20:1 dr. Notably, the method maintained its yield and enantioselectivity integrity even in a gram-scale amplification experiment. For example, the product with substituents on aromatics were obtained in 90% yield with 91% ee and >20:1 dr. Its absolute configuration was established through X-ray single-crystal diffraction analysis, and a plausible reaction mechanism was proposed.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29204856