Synthesis of 4-Oxoisoxazoline N-Oxides via Pd-Catalyzed Cyclization of Propargylic Alcohols with tert-Butyl Nitrite

Autor:	Kai-Wen Feng, Pan-Feng Yuan, Ran Fang, Wen-Long Lei, Yong-Liang Ban, Qiang Liu
Rok vydání:	2019
Předmět:	Tert butyl 010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Density functional theory Physical and Theoretical Chemistry Nitrite
Zdroj:	Organic Letters. 21:3131-3135
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.9b00811
Popis:	A cyclization of propargylic alcohols with tert-butyl nitrite at room temperature in air was achieved using Pd(OAc)2 as catalyst. The first reported 4-oxoisoxazoline N-oxides could be directly accessed from a range of multisubstituted propargylic alcohols in moderate to excellent yields under mild conditions. Density functional theory calculations indicated that the reaction proceeds through a palladium-catalyzed NO2 addition that efficiently generates a ketoxime radical, which eventually produces 4-oxoisoxazoline N-oxide.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e3b5e208ce5b2b6312d2592b7bc2afc2 https://doi.org/10.1021/acs.orglett.9b00811 Zobrazit plný text záznamu