Catalytic Diastereo‐ and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen

We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox‐neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2‐diols (as a mixture of diastereomers) couple to forge two C−N bonds i...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2021-08, Vol.60 (34), p.18599-18604
Main Authors: Pan, Hui‐Jie, Lin, Yamei, Gao, Taotao, Lau, Kai Kiat, Feng, Wei, Yang, Binmiao, Zhao, Yu
Format: Article
Language:English
Subjects:
Amination
Aniline
Catalysis
Chemical synthesis
chiral diamines
cooperative catalysis
Diamines
Diastereoisomers
Diols
double amination of diols
enantioselectivity
Iridium
Lewis acid
Phosphoric acid
redox-neutral
Ruthenium
Stereoselectivity
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Summary:We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox‐neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2‐diols (as a mixture of diastereomers) couple to forge two C−N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co‐catalyzed procedure, the first enantioconvergent double amination of racemic 1,2‐diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2‐diols (as a mixture of diastereomers) couple to forge two C−N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co‐catalyzed procedure, enantioconvergent double amination of racemic 1,2‐diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202101517