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

He-Yuan Bai, Fu-Xin Tan, Tuan-Qing Liu, Guo-Dong Zhu, Jin-Miao Tian, Tong-Mei Ding, Zhi-Min Chen and Shu-Yu Zhang ()
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He-Yuan Bai: Shanghai Jiao Tong University
Fu-Xin Tan: Shanghai Jiao Tong University
Tuan-Qing Liu: Shanghai Jiao Tong University
Guo-Dong Zhu: Shanghai Jiao Tong University
Jin-Miao Tian: Shanghai Jiao Tong University
Tong-Mei Ding: Shanghai Jiao Tong University
Zhi-Min Chen: Shanghai Jiao Tong University
Shu-Yu Zhang: Shanghai Jiao Tong University

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract 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.

Date: 2019
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DOI: 10.1038/s41467-019-10858-x

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