Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles

被引:56
作者
Liu, Kang [1 ]
Xiong, Yong [1 ]
Wang, Zuo-Fei [1 ]
Tao, Hai-Yan [1 ]
Wang, Chun-Jiang [1 ,2 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 230012, Peoples R China
关键词
NICOTINIC ACETYLCHOLINE-RECEPTORS; ASYMMETRIC 3+2 CYCLOADDITION; HIGHLY EFFICIENT; ENANTIOSELECTIVE ADDITION; 1,6-MICHAEL ADDITION; BINDING-AFFINITY; FACILE ACCESS; CONSTRUCTION; EPIBOXIDINE; ANALOGS;
D O I
10.1039/c6cc03169b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unprecedented Ag(I)-catalyzed ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford heterocycles bearing both methylisoxazole and pyrrolidine moieties. The endo- and exo-cycloadducts were obtained in good yields with excellent stereoselectivities, assisted by Bu-t-Phosferrox and phosphoramidite as chiral ligands, respectively.
引用
收藏
页码:9458 / 9461
页数:4
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