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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Bibliographic Details
Published in:Organic letters 2020-03, Vol.22 (6), p.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
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Language:English
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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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00659