Enantioselective Synthesis of Isoxazoline N-Oxides via Pd-Catalyzed Asymmetric Allylic Cycloaddition of Nitro-Containing Allylic Carbonates

Can Zhao; Babar Hussain Shah; Ijaz Khan; Yuhe Kan; Yong Jian Zhang

doi:10.1021/acs.orglett.9b03443

Enantioselective Synthesis of Isoxazoline N-Oxides via Pd-Catalyzed Asymmetric Allylic Cycloaddition of Nitro-Containing Allylic Carbonates

Org Lett. 2019 Nov 15;21(22):9045-9049. doi: 10.1021/acs.orglett.9b03443. Epub 2019 Nov 7.

Authors

Can Zhao¹, Babar Hussain Shah¹, Ijaz Khan¹, Yuhe Kan², Yong Jian Zhang¹

Affiliations

¹ School of Chemistry and Chemical Engineering, and Shanghai Key Laboratory of Electrical Insulation and Thermal Aging , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , PR China.
² Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering , Huaiyin Normal University , Huaian 223300 , PR China.

PMID: 31697086
DOI: 10.1021/acs.orglett.9b03443

Abstract

A useful method for the enantioselective preparation of isoxazoline N-oxides via Pd-catalyzed asymmetric allylic cycloaddition of nitro-containing allylic carbonates has been developed. By using palladium complex in situ generated from Pd₂(dba)₃·CHCl₃ and phosphoramidite L2 as a catalyst under mild conditions, the transformation afforded vinylated isoxazoline N-oxides in high yields with acceptably high enantioselectivities.