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Enantioselective Metal-Catalyzed Reductive Coupling of Alkynes with Carbonyl Compounds and Imines: Convergent Construction of Allylic Alcohols and Amines.

作者信息

Ortiz Eliezer, Shezaf Jonathan, Chang Yu-Hsiang, Krische Michael J

机构信息

University of Texas at Austin, Department of Chemistry, Welch Hall (A5300), 105 E 24 St., Austin, TX 78712, USA.

出版信息

ACS Catal. 2022 Jul 15;12(14):8164-8174. doi: 10.1021/acscatal.2c02444. Epub 2022 Jun 23.

DOI:10.1021/acscatal.2c02444
PMID:37082110
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10112658/
Abstract

The use of alkynes as vinylmetal pronucleophiles in intermolecular enantioselective metal-catalyzed carbonyl and imine reductive couplings to form allylic alcohols and amines is surveyed. Related hydrogen auto-transfer processes, wherein alcohols or amines serve dually as reductants and carbonyl or imine proelectrophiles, also are cataloged, as are applications in target-oriented synthesis. These processes represent an emerging alternative to the use of stoichiometric vinylmetal reagents or Nozaki-Hiyama-Kishi (NHK) reactions in carbonyl and imine alkenylation.

摘要

相似文献

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Enantioselective Metal-Catalyzed Reductive Coupling of Alkynes with Carbonyl Compounds and Imines: Convergent Construction of Allylic Alcohols and Amines.

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[9]
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本文引用的文献

[1]
Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne.

J Am Chem Soc. 2022-5-18

[2]
Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines.

Nat Commun. 2021-10-7

[3]
Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer.

J Am Chem Soc. 2021-10-13

[4]
From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

ACS Catal. 2021-5-7

[5]
Highly Regio- and Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis.

J Am Chem Soc. 2021-5-19

[6]
Nickel-Catalyzed Enantioselective α-Alkenylation of -Sulfonyl Amines: Modular Access to Chiral α-Branched Amines.

J Am Chem Soc. 2021-3-24

[7]
A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction.

Org Lett. 2020-3-12

[8]
Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Org Lett. 2019-6-14

[9]
Versatile Cobalt-Catalyzed Enantioselective Entry to Boryl-Functionalized All-Carbon Quaternary Stereogenic Centers.

J Am Chem Soc. 2018-8-29

[10]
Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Chem Rev. 2018-6-13

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