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分子间金属催化的二烯、丙二烯和炔与羰基化合物和亚胺的还原偶联。

Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

机构信息

Department of Chemistry , University of Texas at Austin , Welch Hall A5300, 105 East 24th Street , Austin , Texas 78712 , United States.

出版信息

Chem Rev. 2018 Jun 27;118(12):6026-6052. doi: 10.1021/acs.chemrev.8b00213. Epub 2018 Jun 13.

DOI:10.1021/acs.chemrev.8b00213

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6203947/

Abstract

Metal-catalyzed reductive coupling has emerged as an alternative to the use of stoichiometric organometallic reagents in an increasingly diverse range of carbonyl and imine additions. In this review, the use of diene, allene, and enyne pronucleophiles in intermolecular carbonyl and imine reductive couplings are surveyed, along with related hydrogen autotransfer processes.

摘要

金属催化的还原偶联已成为替代使用化学计量有机金属试剂的一种方法，在越来越多的羰基和亚胺加成反应中得到了应用。在这篇综述中，调查了二烯、丙二烯和炔烃前体亲核试剂在分子间羰基和亚胺还原偶联中的应用，以及相关的氢自动转移过程。

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本文引用的文献

[1]

Diene hydroaminomethylation ruthenium-catalyzed C-C bond forming transfer hydrogenation: beyond carbonylation.

Chem Sci. 2016-1-1

[2]

Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

J Am Chem Soc. 2018-5-30

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Reductive C-C Coupling Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Curr Opin Green Sustain Chem. 2017-10

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Angew Chem Int Ed Engl. 1999-2-1

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Asymmetric Construction of Fluoroalkyl Tertiary Alcohols through a Three-Component Reaction of (Bpin), 1,3-Enynes, and Fluoroalkyl Ketones Catalyzed by a Copper(I) Complex.

Org Lett. 2018-2-8

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A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

J Am Chem Soc. 2018-2-2

[7]

2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

J Am Chem Soc. 2018-1-4

[8]

Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO.

J Am Chem Soc. 2017-11-10

[9]

Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Angew Chem Int Ed Engl. 2018-2-6

[10]

Stereochemical Characterization of Polyketide Stereotriads Synthesized via Hydrogen-Mediated Asymmetric syn-Crotylation.

J Org Chem. 2017-10-10

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