Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of para-Quinone Methides and Azlactones

Autor:	Xin Li, Chen Yang, Kai-Xue Xie, Zhi-Pei Zhang, Man Li
Rok vydání:	2017
Předmět:	chemistry.chemical_compound chemistry 010405 organic chemistry Organic Chemistry Enantioselective synthesis Organic chemistry Para-quinone Stereoselectivity 010402 general chemistry 01 natural sciences Phosphoric acid 0104 chemical sciences Catalysis
Zdroj:	The Journal of Organic Chemistry. 83:364-373
ISSN:	1520-6904 0022-3263
Popis:	A chiral phosphoric acid-catalyzed approach constructing dihydrocoumarin motifs by the addition of azlactones to para-quinone methides (p-QMs) was developed. The reaction proceeded smoothly with a wide range of p-QMs and azlactones to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the stereoselectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e75e4a0471e46e13f3aa8b3f91047316 https://doi.org/10.1021/acs.joc.7b02750 Zobrazit plný text záznamu