Gold-Catalyzed Intermolecular Ynamide Amination-Initiated Aza-Nazarov Cyclization: Access to Functionalized 2-Aminopyrroles

被引:96
|
作者
Shu, Chao [1 ,2 ]
Wang, Yong-Heng [1 ,2 ]
Shen, Cang-Hai [1 ,2 ]
Ruan, Peng-Peng [1 ,2 ]
Lu, Xin [1 ,2 ]
Ye, Long-Wu [1 ,2 ,3 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
FORMAL 3+2 CYCLOADDITION; POLYSUBSTITUTED PYRROLES; NUCLEOPHILIC NITRENOIDS; SELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; CARBENES; DERIVATIVES; OXIDATION; 2H-AZIRINES; GENERATION;
D O I
10.1021/acs.orglett.6b01503
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel gold-catalyzed intermolecular ynamide amination-initiated aza-Nazarov cyclization has been developed, allowing the facile and efficient synthesis of various 2-aminopyrroles in moderate to good yields. Furthermore, a mechanistic rationale for this tandem sequence, especially for the observed high regioselectivity, is also well supported by DFT (density functional theory) computations. The high flexibility, broad substrate scope, and mild nature of this reaction render it a viable alternative for the construction of 2-aminopyrroles.
引用
收藏
页码:3254 / 3257
页数:4
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