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Machine‐Assisted Preparation of a Chiral Diamine Ligand Library and In Silico Screening Using Ab Initio Structural Parameters for Heterogeneous Chiral Catalysts
Author(s) -
Kuremoto Tatsuya,
Sadatsune Ren,
Yasukawa Tomohiro,
Yamashita Yasuhiro,
Kobayashi Shū
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100798
Subject(s) - chemistry , reductive amination , ab initio , ligand (biochemistry) , catalysis , diamine , amination , combinatorial chemistry , in silico , flow chemistry , computational chemistry , organic chemistry , biochemistry , receptor , gene
A ligand library containing 31 chiral diamines was synthesized using a flow‐based semiautomatic reductive amination system. These ligands were evaluated in a continuous‐flow asymmetric 1,4‐addition reaction with a heterogeneous Ni catalyst. Based on the experimental results of ab initio DFT calculations, a prediction model for enantioselectivities was successfully constructed. Furthermore, virtual screening of possible ligands was conducted to identify promising structures, which showed good enantioselectivities in experiments.