Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination

Nonbiaryl N-C atropisomer is an important structural scaffold, which is present in natural products, medicines and chiral ligands. However the direct enantioselective C-H amination to access optically pure N-C atropisomer is still difficult and rare. Here we report a π-π interaction and dual H-bond...

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Published inNature communications Vol. 10; no. 1; pp. 3063 - 9
Main Authors Bai, He-Yuan, Tan, Fu-Xin, Liu, Tuan-Qing, Zhu, Guo-Dong, Tian, Jin-Miao, Ding, Tong-Mei, Chen, Zhi-Min, Zhang, Shu-Yu
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 11.07.2019
Nature Publishing Group
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Summary:Nonbiaryl N-C atropisomer is an important structural scaffold, which is present in natural products, medicines and chiral ligands. However the direct enantioselective C-H amination to access optically pure N-C atropisomer is still difficult and rare. Here we report a π-π interaction and dual H-bond concerted control strategy to develop the chiral phosphoric acids (CPAs) catalyzed direct intermolecular enantioselective C-H amination of N-aryl-2-naphthylamines with azodicarboxylates as amino sources for the construction of atroposelective naphthalene-1,2-diamines. This type of N-C atropisomers is stabilized by intramolecular hydrogen bond and the method features a broad range of substrates, high yields and ee values, providing a strategy to chirality transfer via the modification of N-C atropisomers. Atropisomers with a chiral C-N axis are useful for natural products synthesis and as ligands in asymmetric catalysis. Here, the authors reportt a π-π interaction and dual H-bond concerted control strategy in enantioselective C-H amination affording configurationally stable N-C atropisomers.
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ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-019-10858-x