Asymmetric [4+2] cycloaddition of azlactones with dipolar copper–allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives

Autor:	Qing-Xian Hu, Jie-Qiang Yu, Bing-Bing Sun, Jia-Ming Hu, Xing-Wang Wang, Jun Jia
Rok vydání:	2019
Předmět:	010405 organic chemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element Optically active 010402 general chemistry 01 natural sciences Biochemistry Copper Combinatorial chemistry Cycloaddition 0104 chemical sciences Catalysis Dipole chemistry Drug Discovery
Zdroj:	Tetrahedron Letters. 60:1967-1970
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2019.06.041
Popis:	In this paper, a pybox-copper catalyzed enantioselective decarboxylative [4+2] cycloaddition reaction of ethynyl benzoxazinanones with azlactones has been developed, which provides optically active 3,4-dihydroquinolin-2-ones in high yields with good enantioselectivities and diastereoselectivities. In this transformation, the chiral dipolar copper–allenylidene intermediates are kinetically generated via decarboxylative ethynyl benzoxazinanones, followed by the attack of the enolate azlactones to form enantiomerically enriched 3,4-dihydroquinolin-2-one structures.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::db7b542349c9a3d6d98bf6b34866aead https://doi.org/10.1016/j.tetlet.2019.06.041 Zobrazit plný text záznamu Full Text from ScienceDirect