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 -2,2-difluoroethylbenzothiophenone imines was developed. This approach efficiently afforded dispiro[benzothiophenone-indandione-pyrrolidine]s, featuring three stereocenters, in 84-98% yields wi...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2024-10, Vol.29 (20), p.4856
Main Authors: Liu, Hong-Yan, Du, Da-Ming
Format: Article
Language:English
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
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Summary:An organocatalytic enantioselective [3+2] cycloaddition reaction involving 2-arylidene-1,3-indandiones and -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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29204856