Chiral Bronsted Acid-Catalyzed Asymmetric 1,4-Addition of Benzofuran-Derived Azadienes with 3-Substituted indoles

被引:24
作者
Zhou, Ji [1 ]
Li, Tian-Zhen [1 ]
Sun, Yu-Wen [1 ]
Du, Bai-Xiang [1 ]
Tan, Wei [1 ]
Shi, Feng [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
关键词
organocatalysis; enantioselectivity; asymmetric synthesis; chiral phosphoric acid; indole; ELECTRONIC CIRCULAR-DICHROISM; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; PHOSPHORIC-ACID; ABSOLUTE-CONFIGURATION; CONJUGATE ADDITION; OPTICAL ROTATIONS; NATURAL-PRODUCTS; CYCLOADDITION; CONSTRUCTION;
D O I
10.1002/cctc.202000810
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A chiral phosphoric acid-catalyzed asymmetric 1,4-addition of benzofuran-derived azadienes with 3-substituted indoles has been established, which offered enantioenriched tri(hetero)arylmethane products in generally good yields (up to 98 %) and high enantioselectivities (up to 99 : 1 er). This reaction has not only realized the application of chiral phosphoric acid as a competent catalyst in the asymmetric transformations of benzofuran-derived azadienes, but also has accomplished the task of developing chiral Bronsted acid-catalyzed asymmetric 1,4-additions of benzofuran-derived azadienes, which will enrich the research contents of chiral phosphoric acid catalysis and the chemistry of benzofuran-derived azadienes.
引用
收藏
页码:4862 / 4870
页数:9
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