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羰基烯丙基化和巴豆基化：历史回顾、与聚酮化合物合成的相关性以及对映选择性钌催化氢自动转移过程的发展

Carbonyl Allylation and Crotylation: Historical Perspective, Relevance to Polyketide Synthesis, and Evolution of Enantioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer Processes.

作者信息

Ortiz Eliezer, Saludares Connor, Wu Jessica, Cho Yoon, Santana Catherine G, Krische Michael J

机构信息

University of Texas at Austin, Department of Chemistry. 105 E 24 St. (A5300), Austin, Tx 78712-1167 (USA).

出版信息

Synthesis (Stuttg). 2023 May;55(10):1487-1496. doi: 10.1055/s-0042-1751420. Epub 2023 Feb 20.

DOI:10.1055/s-0042-1751420

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10569400/

Abstract

The evolution of methods for carbonyl allylation and crotylation of alcohol proelectrophiles culminating in the design of iodide-bound ruthenium-JOSIPHOS catalysts is prefaced by a brief historical perspective on asymmetric carbonyl allylation and its relevance to polyketide construction. Using gaseous allene or butadiene as precursors to allyl- or crotylruthenium nucleophiles, respectively, new capabilities for carbonyl allylation and crotylation have been unlocked, including stereo- and site-selective methods for the allylation and crotylation of 1,3-diols and related polyols.

摘要

醇亲电试剂羰基烯丙基化和巴豆酰化方法的发展最终促成了碘结合钌-JOSIPHOS催化剂的设计，在此之前先简要回顾了不对称羰基烯丙基化及其与聚酮化合物构建的相关性。分别使用气态丙二烯或丁二烯作为烯丙基钌或巴豆基钌亲核试剂的前体，羰基烯丙基化和巴豆酰化展现出了新的能力，包括1,3-二醇及相关多元醇烯丙基化和巴豆酰化的立体和位点选择性方法。

相似文献

[1]

Carbonyl Allylation and Crotylation: Historical Perspective, Relevance to Polyketide Synthesis, and Evolution of Enantioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer Processes.

Synthesis (Stuttg). 2023-5

[2]

Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° vs 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction.

ACS Catal. 2023-2-3

[3]

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Angew Chem Int Ed Engl. 2022-12-5

[4]

Ruthenium-Catalyzed Butadiene-Mediated Crotylation and Oxazaborolidine-Catalyzed Vinylogous Mukaiyama Aldol Reaction for The Synthesis of C1-C19 and C23-C35 of Neaumycin B.

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[5]

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[8]

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[9]

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[10]

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[5]

β-Hydroxy Esters as Malonic Semialdehyde Proelectrophiles in Enantioselective Butadiene-Mediated Crotylation: Total Synthesis of Octalactins A and B.

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[7]

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本文引用的文献

[1]

Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° vs 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction.

ACS Catal. 2023-2-3

[2]

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

ACS Catal. 2022-7-15

[3]

Functional characterization of prokaryotic dark matter: the road so far and what lies ahead.

Curr Res Microb Sci. 2022-8-7

[4]

Historical perspective on ruthenium-catalyzed hydrogen transfer and survey of enantioselective hydrogen auto-transfer processes for the conversion of lower alcohols to higher alcohols.

Chem Sci. 2022-10-26

[5]

Ruthenium-Catalyzed Butadiene-Mediated Crotylation and Oxazaborolidine-Catalyzed Vinylogous Mukaiyama Aldol Reaction for The Synthesis of C1-C19 and C23-C35 of Neaumycin B.

Angew Chem Int Ed Engl. 2022-12-23

[6]

Stereo- and Site-Selective Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by Methylallene and Butadiene.

Angew Chem Int Ed Engl. 2022-12-5

[7]

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

[8]

Total Synthesis of the Acetyl CoA Carboxylase Inhibitor Soraphen A: Asymmetric Tsuji Reduction Enables Successive Olefin Metathesis.

J Am Chem Soc. 2022-1-19

[9]

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

[10]

Vast (but avoidable) underestimation of global biodiversity.

PLoS Biol. 2021-8

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