Tunable Diastereoselective Desymmetrization of Cyclohexadienones Triggered by Copper-Catalyzed Three-Component Coupling Reaction

被引：26
作者：
Anugu, Raghunath Reddy
Chegondi, Rambabu [1 ]
机构：
[1] CSIR, Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 13期
关键词：
ENANTIOSELECTIVE SYNTHESIS; MULTICOMPONENT REACTIONS; ARYLATIVE CYCLIZATION; ASYMMETRIC-SYNTHESIS; HECK REACTION; DEAROMATIZATION; TRANSFORMATIONS; SULFONYL; ALKYNE;
D O I：
10.1021/acs.joc.7b00936
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Catalytic tandem diastereoselective desymmetrization of cyclohexadienone-containing 1,6-enynes has been achieved through copper-catalyzed [3 + 2]-cycloaddition followed by ketenimine formation and subsequent intramolecular conjugate addition. The cascade reaction provides cis-hydrobenzofurans in good yields with excellent diastereoselectivity. The exo- or endo-selectivity of bicyclic scaffolds depends on the selection of the base in the reaction. In addition, N-tethered bicyclic products further transformed into tricyclic compounds via intramolecular Michael addition.
引用
收藏
页码：6786 / 6794
页数：9
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