Organocatalytic Asymmetric Cyclopropanation of 3-Acylcoumarins with 3-Halooxindoles: Access to Spirooxindole-cyclopropa[c]coumarin Compounds

Autor:	Jian-Qiang Zhao, Chuan-Wen Lei, Zhen-Hua Wang, Wei-Cheng Yuan, Yong You
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Cyclopropanation Ylide Stereochemistry Organic Chemistry Intramolecular cyclization Enantioselective synthesis Coumarin Catalysis Stereocenter
Zdroj:	The Journal of Organic Chemistry. 86:2534-2544
ISSN:	1520-6904 0022-3263
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::28c850a1b964d54a7da9daee11aca1c6 https://doi.org/10.1021/acs.joc.0c02653 Zobrazit plný text záznamu