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

Autor:	Hong-Yan Liu, Da-Ming Du
Jazyk:	angličtina
Rok vydání:	2024
Předmět:	asymmetric catalysis 2-arylidene-1 3-indandione benzothiophenone thiourea squaramide spirocyclic compounds Organic chemistry QD241-441
Zdroj:	Molecules, Vol 29, Iss 20, p 4856 (2024)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules29204856
Popis:	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.
Databáze:	Directory of Open Access Journals
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