Organocatalytic Asymmetric [2+4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides

被引：6

作者：

Liu, Si-Jia ^{[1
]}

Tu, Man-Su ^{[1
]}

Liu, Kai-Yue ^{[1
]}

Chen, Jia-Yi ^{[2
]}

Ni, Shao-Fei ^{[2
]}

Zhang, Yu-Chen ^{[1
]}

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China

[2] Shantou Univ, Dept Chem, Key Lab Preparat & Applicat Ordered Struct Mat Gu, Shantou 515063, Peoples R China

来源：

MOLECULES | 2021年 / 26卷 / 21期

基金：

中国国家自然科学基金;

关键词：

vinylindoles; cycloaddition; ortho-quinone methide; chiral phosphoric acid; asymmetric organocatalysis; DIELS-ALDER REACTIONS; BRONSTED ACID; ENANTIOSELECTIVE ADDITION; PHOSPHORIC-ACID; 4+2 ANNULATION; CONSTRUCTION; CATALYSIS; CYCLIZATIONS; ACCESS; 2-INDOLYLMETHANOLS;

D O I：

10.3390/molecules26216751

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.

引用

页数：22

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