Organocatalytic Atroposelective Arylation of 2‐Naphthylamines as a Practical Approach to Axially Chiral Biaryl Amino Alcohols

The first phosphoric acid catalyzed direct arylation of 2‐naphthylamines with iminoquinones for the atroposelective synthesis of axially chiral biaryl amino alcohols has been developed. This reaction constitutes a highly functional‐group‐tolerant route for the rapid construction of enantioenriched a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-12, Vol.56 (51), p.16308-16312
Main Authors: Chen, Ye‐Hui, Qi, Liang‐Wen, Fang, Fang, Tan, Bin
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
amines
amino alcohols
arylation
Atomic structure
atroposelectivity
Chemical synthesis
Enantiomers
Nucleophiles
organocatalysis
Phosphoric acid
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Summary:The first phosphoric acid catalyzed direct arylation of 2‐naphthylamines with iminoquinones for the atroposelective synthesis of axially chiral biaryl amino alcohols has been developed. This reaction constitutes a highly functional‐group‐tolerant route for the rapid construction of enantioenriched axially chiral biaryl amino alcohols, and is a rare example of 2‐naphthylamines acting as nucleophiles in an organocatalytic enantioselective transformation. Furthermore, the products, which feature various halogen atoms, provide access to structurally diverse axially chiral amino alcohols through further transformations. The phosphoric acid catalyzed direct arylation of 2‐naphthylamines with iminoquinones enables the atroposelective synthesis of axially chiral biaryl amino alcohols. Many functional groups are tolerated in this reaction, and it is a rare example of 2‐naphthylamines acting as nucleophiles in an organocatalytic enantioselective transformation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201710537