Organocatalytic Enantioselective Construction of Heterocycle-Substituted Styrenes with Chiral Atropisomerism

被引：52

作者：

Li, Quan-Zhe ^{[1
,2
]}

Lian, Peng-Fei ^{[1
,2
]}

Tan, Fu-Xin ^{[1
,2
]}

Zhu, Guo-Dong ^{[1
,2
]}

Chen, Chao ^{[1
,2
]}

Hao, Yu ^{[1
,2
]}

Jiang, Wei ^{[1
,2
]}

Wang, Xun-Hui ^{[1
,2
]}

Zhou, Jia ^{[1
,2
]}

Zhang, Shu-Yu ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engineer Chiral Drugs, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Shanghai 200240, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 06期

关键词：

DYNAMIC KINETIC RESOLUTION; AXIAL CHIRALITY; ATROPOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; 4+2 CYCLOADDITION; QUINONE METHIDES; CONVERSION; BIARYLS; ARYLATION; CATALYSIS;

D O I：

10.1021/acs.orglett.0c00659

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a novel pi-pi interaction and dual H-bond concerted control strategy to construct axially chiral naphthylamine heterocycles. With ortho-alkynyl-naphthylamines as the electrophile, indoles and 4-hydroxycoumarins were efficiently employed to construct axially chiral skeletons in good yields and with excellent enantioselectivities (up to 97% enantiomeric excess). Furthermore, the resulting products could be converted to potential squaramides featuring organic catalysts.

引用

页码：2448 / 2453

页数：6

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