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手性磷酸作为有机催化不对称转移氢化的通用工具。

Chiral Phosphoric Acids as Versatile Tools for Organocatalytic Asymmetric Transfer Hydrogenations.

作者信息

Pálvölgyi Ádám Márk, Scharinger Fabian, Schnürch Michael, Bica-Schröder Katharina

机构信息

Institute of Applied Synthetic Chemistry TU Wien Getreidemarkt Vienna, 9/163 1060 Wien Austria.

出版信息

European J Org Chem. 2021 Oct 14;2021(38):5367-5381. doi: 10.1002/ejoc.202100894.

DOI:10.1002/ejoc.202100894
PMID:34819797
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8597106/
Abstract

Herein, recent developments in the field of organocatalytic asymmetric transfer hydrogenation (ATH) of C=N, C=O and C=C double bonds using chiral phosphoric acid catalysis are reviewed. This still rapidly growing area of asymmetric catalysis relies on metal-free catalysts in combination with biomimetic hydrogen sources. Chiral phosphoric acids have proven to be extremely versatile tools in this area, providing highly active and enantioselective alternatives for the asymmetric reduction of α,β-unsaturated carbonyl compounds, imines and various heterocycles. Eventually, such transformations are more and more often used in multicomponent/cascade reactions, which undoubtedly shows their great synthetic potential and the bright future of organocatalytic asymmetric transfer hydrogenations.

摘要

本文综述了使用手性磷酸催化对C=N、C=O和C=C双键进行有机催化不对称转移氢化（ATH）领域的最新进展。这个仍在迅速发展的不对称催化领域依赖于无金属催化剂与仿生氢源的结合。手性磷酸已被证明是该领域极为通用的工具，为α,β-不饱和羰基化合物、亚胺和各种杂环的不对称还原提供了高活性和对映选择性的替代方法。最终，此类转化越来越多地用于多组分/串联反应中，这无疑显示了它们巨大的合成潜力以及有机催化不对称转移氢化的光明前景。

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J Org Chem. 2019 Jun 21;84(12):8300-8308. doi: 10.1021/acs.joc.9b00985. Epub 2019 Jun 5.
9
Chiral Brønsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane.使用1-氢硅氮烷的手性布朗斯特酸催化无金属不对称直接还原胺化反应
J Org Chem. 2019 May 3;84(9):5021-5026. doi: 10.1021/acs.joc.8b03073. Epub 2019 Apr 22.
10
Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1 H)-ones through Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines.通过 2-羟基嘧啶的有机催化转移氢化反应，对映选择性合成 3,4-二氢嘧啶-2(1H)-酮。
J Org Chem. 2019 Apr 5;84(7):4435-4442. doi: 10.1021/acs.joc.8b03128. Epub 2019 Mar 21.