Catalytic asymmetric (4 + 1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides

Autor:	Xia Fan, Jinghua Luo, Zhengjie He, Rongshun Chen, Jie Han, Junyu Gong
Rok vydání:	2019
Předmět:	Allylic rearrangement Annulation 010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Cinnamates Organic chemistry Ammonium Stereoselectivity Physical and Theoretical Chemistry
Zdroj:	Organic & Biomolecular Chemistry. 17:6989-6993
ISSN:	1477-0539 1477-0520
DOI:	10.1039/c9ob01058k
Popis:	An asymmetric (4 + 1) annulation of α-nitro cinnamates with Morita-Baylis-Hillman (MBH) acetates catalyzed by α-isocupreine is reported. It provides chiral isoxazoline N-oxides in moderate to good yields with 88-99% ee, and represents the first catalytic asymmetric (4 + 1) annulation of activated nitroalkenes with in situ generated ammonium ylides. It also affords a practical and efficient access to chiral isoxazoline N-oxides.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c184300b4fe4135774c16abd3ab90cfc https://doi.org/10.1039/c9ob01058k Zobrazit plný text záznamu