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Catalytic Diastereo‐ and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen
Author(s) -
Pan HuiJie,
Lin Yamei,
Gao Taotao,
Lau Kai Kiat,
Feng Wei,
Yang Binmiao,
Zhao Yu
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202101517
Subject(s) - vicinal , chemistry , diastereomer , catalysis , ruthenium , reductive amination , amination , organic chemistry , lewis acids and bases , combinatorial chemistry
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.