Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

被引：12
|
作者：
Fernandes, Rodney A. [1 ]
Gangani, Ashvin J. [1 ]
Panja, Arpita [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
关键词：
ALLYLIC SUBSTITUTION; ISOXAZOLINE; DERIVATIVES; MIGRATION; LIGAND; ACIDS;
D O I：
10.1021/acs.orglett.1c01897
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed p-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.
引用
收藏
页码：6227 / 6231
页数：5
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