4.8 Article

Amine-Release Annulation of Enaminones: Bimetallic Co-Catalytic Synthesis of Cyclopentadienes from Alkynes

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

Site-Selective C-H Allylation of Alkanes: Facile Access to Allylic Quaternary sp(3)-Carbon Centers

Yong Yang et al.

Summary: This study presents a carbene strategy using vinyl-N-triftosylhydrazones as a versatile allylating reagent for the direct assembly of allylic quaternary sp(3)-carbon centers from low-cost alkane feedstocks. The reaction showed excellent site selectivity for tertiary C-H bonds, broad scope, and high efficiency, making it a convenient alternative to the Trost-Tsuji allylation reaction. Experimental and computational studies were conducted to understand the mechanism and origin of site- and chemoselectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Physical

Rhodium/Amine Dual Catalytic System for Reassembling CC Bonds of Conjugated Alkynes with Cyclopropenes via Cutting/ Insertion Cascade

Jie Chen et al.

Summary: In this study, we describe an efficient amine/Rh(II) dual catalytic system that enables the reassembly of conjugated alkynes with cyclopropenes, resulting in the construction of alpha-vinyldicarbonyl derivatives under mild reaction conditions. This cascade platform offers high atom and step economies, and is compatible with a broad range of substrates including complex natural and unnatural molecules for late-stage functionalization.

ACS CATALYSIS (2022)

Article Chemistry, Organic

PtI4-catalyzed oxidative and hydrogenative dearomative [3+2] cycloaddition of 1H-indole N-tethered o-alkynylbenzaldehydes

Dandan Shang et al.

Summary: This article describes a synthetic method for the assembly of highly functionalized and structurally challenging cyclohepta[b]indolines. The method involves PtI4-catalyzed oxidative and hydrogenative dearomative [3 + 2] cycloaddition in a single operation. The method exhibits excellent functional group tolerance and is suitable for late-stage modification of complex bioactive natural products and drug molecules.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

Gold-Catalyzed Regioselective Synthesis of Crowded Cyclopentadienes by Migratory Cycloisomerization of Vinylallenes

Olaya Bernardo et al.

Summary: In this study, we successfully reported a regioselective synthesis method for silyl-substituted cyclopentadienyl esters through gold-catalyzed migratory cycloisomerization of silyl-substituted vinylallenes. Additionally, we have identified more straightforward synthesis conditions using the multifaceted nature of the gold catalyst, by reacting propargyl esters and alkynylsilanes.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Ligand-controlled chemoselectivity in gold-catalyzed cascade cyclization of 1,4-diene-tethered 2-alkynylbenzaldehydes

Jichao Chen et al.

Summary: This study presents a method to selectively assemble polycyclic bridged pyrrolidines and azepines using gold(I)-catalyzed cascade annulation, showcasing the divergent product selectivity by controlling the reaction pathway and ligand steric nature of the metal complex. The synthetic utility of this divergent catalytic protocol was demonstrated by modifying structurally complex natural products and drug molecules under mild reaction conditions, highlighting its potential applications in drug synthesis and natural product modification.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

THF-enabled PtBr2-catalyzed desymmetric hydrogenative [3+2] cycloaddition of 2-alkynylbenzaldehyde-tethered cyclohexadienones

Rui Hu et al.

Summary: A THF-enabled PtBr2-catalyzed desymmetric hydrogenative [3 + 2] cycloaddition of 2-alkynylbenzaldehyde-tethered cyclohexadienones has been developed. The protocol provides a highly functionalized 6-7-6 polycyclic skeleton with four contiguous stereocenters in good to excellent yields. The involvement of an in situ formed Pt-bound benzopyrylium species in the cascade reaction pathway and the generation of a metallocarbene species that undergoes hydrogenation with THF as the hydride transfer source are novel findings. The catalytic method also demonstrates its synthetic utility in the late-stage stereoselective modification of steroids.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Gold-Catalyzed Reaction of Propargyl Esters and Alkynylsilanes: Synthesis of Vinylallene Derivatives through a Twofold 1,2-Rearrangement

Olaya Bernardo et al.

Summary: The gold-catalyzed reaction of propargyl esters with alkynylsilanes produces vinylallene derivatives through consecutive [1,2]-acyloxy/[1,2]-silyl rearrangements. This transformation features good yields, full atom-economy, a broad substrate scope, easy scale-up, and low catalyst loadings. The reaction mechanism involves the generation of a gold vinylcarbene intermediate and a type II-Dyotropic rearrangement involving the silyl group and the metal fragment.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Medicinal

Spirocyclic Scaffolds in Medicinal Chemistry

Kerstin Hiesinger et al.

Summary: Spirocyclic scaffolds are widely used in drugs, and the interest in nonplanar bioactive compounds is growing. This article summarizes different synthetic routes to obtain spirocyclic systems, discussing their impact on potency and selectivity, as well as changes in physicochemical properties and ADME in vitro and in vivo.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Homogeneous Gold-Catalyzed Oxidation Reactions

Zhitong Zheng et al.

Summary: Homogeneous gold catalysis has seen significant development since the turn of the millennium, with oxidative gold catalysis being a vibrant subfield delivering valuable synthetic methods. This comprehensive review covers the mechanistic aspects, oxidants, and synthetic applications of oxidative gold catalysis.

CHEMICAL REVIEWS (2021)

Article Chemistry, Organic

Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes

Olaya Bernardo et al.

Summary: This study reports the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, common structural motifs in bioactive compounds. The reaction proceeds with complete regio- and stereoselectivity, with the silyl group serving as a regio- and stereocontrolling element. Additionally, the use of alkynylsilanes as reaction partners yielded skipped enynes through C(sp)-C(sp(3)) coupling.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Impact of the Difluoromethylene Group in the Organocatalyzed Acylative Kinetic Resolution of α,α-Difluorohydrins

Titouan Desrues et al.

Summary: This study reported an enantioselective organocatalyzed acylation of alpha,alpha-difluorohydrins using a commercially available chiral isothiourea, greatly improving the enantioselectivity of the kinetic resolution process through electrostatic fluorine-cation interactions. The method allows for the synthesis of various fluorinated alcohols with exquisite enantiocontrol, such as 4,4-difluoro-1,3-diols, as well as demonstrated compatibility between aromatic and fluorinated groups in providing enantioenriched adducts.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Rh(II)-Catalyzed Alkynylcyclopropanation of Alkenes by Decarbenation of Alkynylcycloheptatrienes

Mauro Mato et al.

Summary: A new two-step methodology has been developed for the synthesis of alkynylcyclopropanes, which avoids the usual problems associated with these substrates under metal catalysis. This approach allows for rapid access to a diverse library of alkynylcyclopropanes, including versatile intermediates that previously required lengthier synthetic approaches. Through experiments and DFT calculations, the complete mechanistic picture for the divergent reactivity of alkynylcycloheptatrienes under metal catalysis has been unveiled, explaining the unique selectivity displayed by rhodium(II) complexes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

(Z)-γ-Alkylidenebutenolide Synthesis through Au(I)-Catalyzed 1,3-Acyloxy Migration and the Carbonyl-Ene Reaction

Pathan Mosim Amin et al.

Summary: A bimetallic protocol has been developed for the synthesis of (Z)-gamma-alkylidenebutenolide compounds from propargyl alpha-ketoesters. This method involves a gold-catalyzed acyloxy migration and a carbonyl-ene cyclization process, with DFT calculations suggesting a dual role for copper salt in facilitating the generation of active gold catalyst and promoting intramolecular carbonyl-ene reaction.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

Cleavage and Reassembly CC Bonds of Ynones to Access Highly Functionalized Ketones

Jiaxin Rong et al.

ACS CATALYSIS (2020)

Article Chemistry, Multidisciplinary

1,1-Digoldallylium Complexes: Diaurated Allylic Carbocations Indicate New Prospects of the Coordination Chemistry of Carbon

Florian F. Mulks et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

Jie Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Gold-Catalyzed Migration of Propargyl Acetate as an Entry into the Total Synthesis of Natural Products

Virginie Mouries-Mansuy et al.

ISRAEL JOURNAL OF CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Zinc-Catalyzed Synthesis of Allylsilanes by Si-H Bond Insertion of Vinyl Carbenoids Generated from Cyclopropenes

Sergio Mata et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

N-Tosylhydrazones: versatile synthons in the construction of cyclic compounds

Ying Xia et al.

CHEMICAL SOCIETY REVIEWS (2017)

Review Chemistry, Multidisciplinary

Cyclometalated Gold(III) Complexes: Synthesis, Reactivity, and Physicochemical Properties

Roopender Kumar et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Reaction of Diazo Compounds with Difluorocarbene: An Efficient Approach towards 1,1-Difluoroolefins

Zhikun Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

New Approaches to the Synthesis of Metal Carbenes

Minqiang Jia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Gold catalysis in total synthesis - recent achievements

Daniel Pflaesterer et al.

CHEMICAL SOCIETY REVIEWS (2016)

Review Chemistry, Multidisciplinary

Asymmetric Catalysis Powered by Chiral Cyclopentadienyl Ligands

Christopher G. Newton et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Chemistry, Multidisciplinary

Intramolecular Cyclopropanation and C-H Insertion Reactions with Metal Carbenoids Generated from Cyclopropenes

Alexis Archambeau et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Article Chemistry, Multidisciplinary

Zinc-Catalyzed Alkene Cyclopropanation through Zinc Vinyl Carbenoids Generated from Cyclopropenes

Maria J. Gonzalez et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Au-Catalyzed Cross-Coupling of Arenes via Double C-H Activation

Xacobe C. Cambeiro et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Multidisciplinary Sciences

Stable gold(III) catalysts by oxidative addition of a carbon-carbon bond

Chung-Yeh Wu et al.

NATURE (2015)

Article Chemistry, Physical

Explanation of Silver Effects in Gold(I)-Catalyzed Hydroalkoxylation of Alkynes

Alexander Zhdanko et al.

ACS CATALYSIS (2015)

Review Chemistry, Multidisciplinary

A Non-Diazo Approach to α-Oxo Gold Carbenes via Gold-Catalyzed Alkyne Oxidation

Liming Zhang

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Article Chemistry, Multidisciplinary

Pd-Catalyzed ring-opening cross-coupling of cyclopropenes with aryl iodides

Hang Zhang et al.

CHEMICAL COMMUNICATIONS (2014)

Review Chemistry, Multidisciplinary

Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles

Huw M. L. Davies et al.

CHEMICAL SOCIETY REVIEWS (2014)

Article Chemistry, Multidisciplinary

Activation of Aryl Halides at Gold(I): Practical Synthesis of (P,C) Cyclometalated Gold(III) Complexes

Johannes Guenther et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Exceptionally fast carbon-carbon bond reductive elimination from gold(III)

William J. Wolf et al.

NATURE CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Gold Catalysis: Highly Functionalized Cyclopentadienes Prepared by Intermolecular Cyclization of Ynamides and Propargylic Carboxylates

Eva Rettenmeier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates

Roohollah Kazem Shiroodi et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Multidisciplinary

Silver Effect in Gold(I) Catalysis: An Overlooked Important Factor

Dawei Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Review Chemistry, Inorganic & Nuclear

Penta-arylcyclopentadienyl complexes

Leslie D. Field et al.

COORDINATION CHEMISTRY REVIEWS (2011)

Article Chemistry, Multidisciplinary

Gold catalysed reactions with cyclopropenes

Juergen T. Bauer et al.

CHEMICAL COMMUNICATIONS (2008)

Review Multidisciplinary Sciences

Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion

Huw M. L. Davies et al.

NATURE (2008)

Article Chemistry, Organic

Contrasteric Diels-Alder reactions of 5-methyl-5-phenylcyclopentadiene

Masaru Ishida et al.

TETRAHEDRON LETTERS (2008)

Article Chemistry, Multidisciplinary

Singlet vinylcarbenes: Spectroscopy and photochemistry

PS Zuev et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Multidisciplinary

Daphnicyclidins A-H, novel hexa- or pentacyclic alkaloids from two species of Daphniphyllum

J Kobayashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)