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

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.

journal_name

Nat Commun

journal_title

Nature communications

authors

Bai HY,Tan FX,Liu TQ,Zhu GD,Tian JM,Ding TM,Chen ZM,Zhang SY

doi

10.1038/s41467-019-10858-x

subject

Has Abstract

pub_date

2019-07-11 00:00:00

pages

3063

issue

1

issn

2041-1723

pii

10.1038/s41467-019-10858-x

journal_volume

10

pub_type

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