Organocatalytic Enantioselective Construction of Heterocycle-Substituted Styrenes with Chiral Atropisomerism

We have developed a novel π–π 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 y...

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Published inOrganic letters Vol. 22; no. 6; pp. 2448 - 2453
Main Authors Li, Quan-Zhe, Lian, Peng-Fei, Tan, Fu-Xin, Zhu, Guo-Dong, Chen, Chao, Hao, Yu, Jiang, Wei, Wang, Xun-Hui, Zhou, Jia, Zhang, Shu-Yu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.03.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
ASYMMETRIC-SYNTHESIS
AXIAL CHIRALITY
4+2 CYCLOADDITION
CONVERSION
QUINONE METHIDES
ATROPOSELECTIVE SYNTHESIS
ARYLATION
DYNAMIC KINETIC RESOLUTION
BIARYLS
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Summary:We have developed a novel π–π 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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00659