Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid

Autor:	Jiye Jeon, Cheol Hong Cheon, So Young Lee, Do Young Park
Rok vydání:	2018
Předmět:	chemistry.chemical_compound chemistry 010405 organic chemistry One pot reaction Organic Chemistry Enantioselective synthesis Estrogen Receptor Modulators 010402 general chemistry 01 natural sciences Combinatorial chemistry Phosphoric acid 0104 chemical sciences Catalysis
Zdroj:	The Journal of Organic Chemistry. 83:12486-12495
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.8b01709
Popis:	A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f067b43d756cb2336a08facfd15869fd https://doi.org/10.1021/acs.joc.8b01709 Zobrazit plný text záznamu