☆ 4.8 Article

Phosphine-Catalyzed [3+2] Cycloaddition of 4,4-Dicyano-2-methylenebut-3-enoates with Benzyl Buta-2,3-dienoate and Penta-3,4-dien-2-one

ACS CATALYSIS (2013)

Journal

ACS CATALYSIS

Volume 3, Issue 4, Pages 507-512

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/cs300751a

Keywords

allenoate; 4,4-dicyano-2-methylenebut-3-enoates; multifunctional chiral phosphines; [3+2] cycloaddition

Categories

Chemistry, Physical

Funding

Shanghai Municipal Committee of Science and Technology [11JC1402600]
National Basic Research Program of China [(973)-2010CB833302]
Fundamental Research Funds for the Central Universities
National Natural Science Foundation of China [21102166, 21072206, 20472096, 20872162, 20672127, 21121062, 20732008]

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

4,4-Dicyano-2-methylenebut-3-enoates are employed in the phosphine-catalyzed [3 + 2] cycloaddition with allenoates for the first time, affording regiospecific [3 + 2]-annulation products in moderate to good yields. The multifunctional chiral thiourea-phosphines having an axially chiral binaphthyl scaffold are effective catalysts for the asymmetric variant of this reaction, giving the alpha-regioisomers in good yields and moderate enantioselectivities.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Organic

Catalyst-free inverse-electron-demand aza-Diels-Alder reaction of 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes: access to polysubstituted tetrahydropyridines

Dezhi Yang, Meng Zhu, Taimin Wang, Yixuan He, Lang Xie, Jiayong Zhang, Bin Cheng

Summary: A catalyst-free and additive-free reaction was developed for the inverse-electron-demand aza-Diels-Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes, providing a highly convenient method to construct polyfunctionalized tetrahydropyridines in high yields. This strategy exhibits advantages such as high efficiency, good functional group tolerance, broad substrate scope, and environmentally friendly conditions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Add to Collection

Article Chemistry, Physical

Iminosugar-Phosphines as Organocatalysts in the [3+2] Cycloaddition of Allenoates and N-Tosylimines

Pilar Elias-Rodriguez, Ana T. Carmona, Antonio J. Moreno-Vargas, Inmaculada Robina

Summary: In this study, iminosugar derivatives containing a pyrrolidine-phosphine moiety were synthesized and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The results demonstrated that under appropriate conditions, 1,2,3,5-tetrasubstituted pyrrolines with high yields and good diastereoselectivities were obtained.

CATALYSTS (2022)

Add to Collection

Article Chemistry, Organic

Stereospecific [3+2] Cycloaddition of Chiral Arylallenes with C,N- Cyclic Azomethine Imines

Xinyu Liu, Zhixin Liu, Yongyi Hu, Kuo-Wei Huang, Manjaly J. Ajitha, De Wang

Summary: A novel alpha,beta-regioselective [3+2] cycloaddition reaction of arylallene with C,N-cyclic azomethine imine is reported. The axial-to-central chirality transfer phenomenon has been disclosed with chiral allenes in the reaction. The wide substrate scope, including different functional groups and natural products, reveals the generality of the methodology. Both experiments and density functional theory calculations have been used to elucidate a plausible mechanism.

ORGANIC LETTERS (2023)

Add to Collection

Article Chemistry, Organic

Sc(OTf)3 catalyzed [3+2]-annulation reaction of donor-acceptor aziridines with methylene exo-glycals: synthesis of chiral carbohydrate-spiro-heterocycles

Jie-Hui Zhang, Cheng-Lin Pan, Huan-Huan Zhang, Peng-Fei Xu, Yong-Chun Luo

Summary: A Sc(OTf)3 catalyzed [3 + 2]-annulation reaction has been developed for the conversion of donor-acceptor aziridines and exo-glycals into carbohydrate-spiro-heterocycles, yielding proline analogues and polycyclic compounds. This reaction also revealed the stereochemistry characteristic of the reaction between racemic D-A aziridines and chiral enolethers.

ORGANIC CHEMISTRY FRONTIERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Hydrophosphinylation of 2-Vinylazaarenes to Access P-Chiral 2-Azaaryl-Ethylphosphine Oxides

Binghui Wang, Yilin Liu, Chenyang Jiang, Zheng Cao, Shanshan Cao, Xiaowei Zhao, Xu Ban, Yanli Yin, Zhiyong Jiang

Summary: Describes a chiral Bronsted acid-catalysed asymmetric hydrophosphinylation of 2-vinylazaarenes by secondary phosphine oxides. P-chiral 2-azaaryl-ethylphosphine oxides are synthesized with high yields and ees, allowing for flexible modulation of substituents. The resulting P-chiral tertiary phosphines from the reduction are confirmed as effective C-1-symmetric chiral 1,5-hybrid P,N-ligands, making these adducts valuable in asymmetric metal catalysis.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Organic

Cooperative Rh/Chiral Phosphoric Acid Catalysis toward the Highly Stereoselective (3+3)-Cycloannulation of Carbonyl Ylides and Indolyl-2-methides

Henning J. Loui, Arun Suneja, Christoph Schneider

Summary: A synthetic method has been developed for the stereoselective (3 + 3)-cycloannulation of in situ generated carbonyl ylides with indolyl-2-methides, resulting in oxa-bridged azepino[1,2-a]indoles in one step. The products, with three stereogenic centers, were obtained with good stereoselectivity and yields, showcasing valuable heterocyclic complexity.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Taming Chiral Quaternary Stereocenters via Remote H-Bonding Stereoinduction in Palladium-Catalyzed (3+2) Cycloadditions

Yu-Qing Xiao, Miao-Miao Li, Zheng-Xin Zhou, Yu-Jie Li, Meng-Yue Cao, Xiao-Peng Liu, Hai-Hua Lu, Li Rao, Liang-Qiu Lu, Andre M. Beauchemin, Wen-Jing Xiao

Summary: This article describes a palladium-catalyzed highly diastereo- and enantioselective (3+2) cycloaddition reaction, which successfully synthesizes a variety of chiral five-membered heterocycles. The key to the success of this reaction is the remote stereoinduction through hydrogen bond, addressing the challenge of generating chiral quaternary stereocenters using substrates with two different acceptors.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Physical

Multifunctional Ag(I)/CAAA-Amidphos Complex-Catalyzed Asymmetric [3+2] Cycloaddition of α-Substituted Acrylamides

Kai-Qiang Zhang, Qi-Fu Deng, Jie Luo, Chu-Liang Gong, Zhi-Gang Chen, Wei Zhong, Shun-Qin Hu, Hai-Fei Wang

Summary: This study successfully developed an asymmetric [3+2] cycloaddition reaction catalyzed by a multifunctional Ag(I)/CAAA-amidphos complex, enabling the high-yield synthesis of chiral pyrrolidines with quaternary stereocenters and bridged dinitrogen heterocycles with excellent enantioselectivity.

ACS CATALYSIS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands

Sundaravel Vivek Kumar, Patrick J. Guiry

Summary: We have developed a facile synthetic route for a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands with central and planar chirality. These ligands showed excellent activities and selectivities in asymmetric reactions, leading to enantioenriched pyrrolidines with high yields.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Organic

Chiral-Boron-Complex-Catalyzed Asymmetric [3+2] Cycloaddition of 2′-Hydroxychalcones with N,N′-Cyclic Azomethine Imines

Guo-Li Chai, En-Ze Yao, Rui-Hao Liu, Junbiao Chang

Summary: In this study, a new catalytic system was reported for the synthesis of N,N'-bicyclic pyrazolidine derivatives with high stereoselectivity. The reaction conditions are mild and efficient, with a broad substrate scope.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Design of 1-Phosphanorbornene Derivatives as Chiral Organocatalysts for Enantioselective (4+2) Annulation Reactions of γ-Benzyl Allenoates

Siming Jia, Mengmeng Ma, Er-Qing Li, Zheng Duan, Francis Mathey

Summary: Two novel diastereoisomeric P-chirogenic phosphine catalysts, JiaPhos, were successfully synthesized from inexpensive starting materials in five chemical operations on a 4.16g scale. These catalysts demonstrated excellent performance in enantioselective (4 + 2) annulations, providing a diverse range of 3,3'-spirocyclic oxindoles with high efficiency and enantioselectivity.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines

Nicolaj Inunnguaq Jessen, Maksimilian Bura, Giulio Bertuzzi, Karl Anker Jorgensen

Summary: An efficient and stereoselective synthesis of chiral cycl[3.2.2]azines has been achieved through the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion catalysis. The method allows for incorporation of diverse enals and the obtained products can undergo selective transformations while retaining stereochemical information established in the [8+2] cycloaddition.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Intramolecular Ynamide-Benzyne (3+2) Cycloadditions

Tsukasa Tawatari, Ritsuki Kato, Riku Kudo, Kiyosei Takasu, Hiroshi Takikawa

Summary: In this study, we report on the intramolecular (3+2) cycloaddition reactions between ynamides and benzyne. These reactions involve the formation of two bonds and are facilitated by using benzyne precursors containing a chlorosilyl group. The intermediate indolium ylide in these reactions exhibits both nucleophilic and electrophilic properties at its C2 atom.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Organic

Phosphine-Catalyzed (3+2) Annulation of γ-Substituted Cinnamic Aldehyde-Derived Morita-Baylis-Hillman Carbonates through Remote Activation

Yue Ren, Wangyu Shi, Yi Tang, Shixiang Piao, Songcheng Yu, Yongjun Wu, Hongchao Guo

Summary: A series of gamma-substituted MBH carbonates were synthesized and reacted with electrophilic exocyclic alkenes through phosphine-catalyzed annulations, resulting in the formation of valuable spirocyclopentenes with moderate to excellent yields and diastereoselectivities. The annulation process tolerates a wide range of MBH carbonates with gamma-hydrogen, alkenyl, and alkynyl substituents. Notably, this annulation involves the beta, gamma, and delta carbons of MBH carbonates, which is unprecedented.

ORGANIC LETTERS (2023)

Add to Collection

Article Chemistry, Applied

Synthesis of Chiral Nine-Membered N-Heterocycles through Silver(I)-Promoted Cycloaddition and Rearrangement from N-Vinyl-α,β-Unsaturated Nitrones with Chiral 3-Propioloyloxazolidin-2-Ones

Xiao-Ting Qin, Ning Zou, Xiao-Ling Cheng, Cui Liang, Dong-Liang Mo

Summary: A variety of chiral nine-membered N-heterocycles were prepared in moderate to good yields with high diastereoselectivity through a silver(I)-catalyzed reaction. Experimental studies showed that the silver catalyst promoted the cycloaddition and rearrangement process, and controlled the stereochemistry of the products.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Regio- and diastereoselective construction of 1′,2′-(dihydrospiro[indoline-3,3′-pyrrol]-2′-yl)acrylates through phosphine-catalyzed [4+1] annulation of Morita-Baylis-Hillman carbonates with oxindole-derived α, β-unsaturated imines

Yu Lei, Xiao-Nan Zhang, Xue-Yan Yang, Qin Xu, Min Shi

RSC ADVANCES (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Catalyst-Dependent Divergent Synthesis of Pyrroles from 3-Alkynyl Imine Derivatives: A Noncarbonylative and Carbonylative Approach

Gen-Qiang Chen, Xiao-Nan Zhang, Yin Wei, Xiang-Ying Tang, Min Shi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Lewis base-catalyzed reactions of cyclopropenones: novel synthesis of mono-or multi-substituted allenic esters

Yuan-Liang Yang, Zhen Zhang, Xiao-Nan Zhang, De Wang, Yin Wei, Min Shi

CHEMICAL COMMUNICATIONS (2014)

Add to Collection

Article Chemistry, Organic

Access to 2'′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones via amino acid derived phosphine-catalyzed asymmetric [4+2] annulation with easily available oxindole-derived α,β-unsaturated imines

Xiao-Nan Zhang, Xiang Dong, Yin Wei, Min Shi

TETRAHEDRON (2014)

Add to Collection

Article Multidisciplinary Sciences

A ribose-functionalized NAD+ with unexpected high activity and selectivity for protein poly-ADP-ribosylation

Xiao-Nan Zhang, Qinqin Cheng, Jingwen Chen, Albert T. Lam, Yanran Lu, Zhefu Dai, Hua Pei, Nikolai M. Evdokimov, Stan G. Louie, Yong Zhang

NATURE COMMUNICATIONS (2019)

Add to Collection

Article Multidisciplinary Sciences

Synthesis of site-specific antibody-drug conjugates by ADP-ribosyl cyclases

Zhefu Dai, Xiao-Nan Zhang, Fariborz Nasertorabi, Qinqin Cheng, Jiawei Li, Benjamin B. Katz, Goar Smbatyan, Hua Pei, Stan G. Louie, Heinz-Josef Lenz, Raymond C. Stevens, Yong Zhang

SCIENCE ADVANCES (2020)

Add to Collection

Article Biochemistry & Molecular Biology

A Bifunctional NAD+ for Profiling Poly-ADP-Ribosylation-Dependent Interacting Proteins

Albert T. Lam, Xiao-Nan Zhang, Valentine V. Courouble, Timothy S. Strutzenberg, Hua Pei, Bangyan L. Stiles, Stan G. Louie, Patrick R. Griffin, Yong Zhang

Summary: Protein poly-ADP-ribosylation is a heterogeneous and dynamic post-translational modification regulated by various factors, participating in biological events and human diseases. Currently, tools are lacking for clearly defining readers and erasers of PARylated proteins. The newly developed bifunctional NAD(+) serves as an important tool for studying cellular interaction networks centered on protein PARylation.

ACS CHEMICAL BIOLOGY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Site-specific antibody-drug conjugates with variable drug-to-antibody-ratios for AML therapy

Zhefu Dai, Xiao-Nan Zhang, Qinqin Cheng, Fan Fei, Tianling Hou, Jiawei Li, Alireza Abdolvahabi, Junji Watanabe, Hua Pei, Goar Smbatyan, Jianming Xie, Heinz-Josef Lenz, Stan G. Louie, Yong Zhang

Summary: A new technology for producing homogeneous ADCs, ARC-ADCs, was developed by utilizing the human CD38 catalytic domain and its derived inhibitor. Through this technology, ADCs with customizable drug-to-antibody ratios (DARs) can be rapidly generated, showing potent activity in killing hCLL-1-positive AML cells. This work provides novel ADC candidates for combating AML and supports ARC-ADC as a versatile approach for producing site-specific ADCs with defined DARs.

JOURNAL OF CONTROLLED RELEASE (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Discovery of an NAD+ analogue with enhanced specificity for PARP1

Xiao-Nan Zhang, Albert T. Lam, Qinqin Cheng, Valentine V. Courouble, Timothy S. Strutzenberg, Jiawei Li, Yiling Wang, Hua Pei, Bangyan L. Stiles, Stan G. Louie, Patrick R. Griffin, Yong Zhang

Summary: Researchers have reported a synthetic NAD(+) compound featuring high activity and specificity for human PARP1, which can be used as an ADP-ribose donor to label and analyze potential protein substrates of endogenous PARP1.

CHEMICAL SCIENCE (2022)

Add to Collection

Article Biochemistry & Molecular Biology

A Poly-ADP-Ribose Polymer-GCSF Conjugate

Qinqin Cheng, Xiao-Nan Zhang, Lei Zhang, Jingwen Chen, Yiling Wang, Yong Zhang

Summary: This study generated PAR polymer-GCSF conjugates through the combination of PAR polymers and human granulocyte colony-stimulating factor (GCSF) protein, which demonstrated excellent in vivo efficacy and have the potential to be used as carriers for therapeutic proteins or peptides with improved pharmacological activities.

BIOMACROMOLECULES (2022)

Add to Collection

Article Biochemistry & Molecular Biology

Synthesis of Bispecific Antibody Conjugates Using Functionalized Poly-ADP-ribose Polymers

Yong Zhang, Qinqin Cheng, Xiao-Nan Zhang, Jiawei Li, Jingwen Chen, Yiling Wang

Summary: In this study, a PAR polymer-based bispecific antibody targeting both HER2 and T-cell CD3 antigens was developed. The conjugate had specific binding to target cells expressing HER2 and CD3, and exhibited potent cytotoxicity against HER2-positive breast cancer cells in the presence of non-activated PBMCs. Functionalized PAR polymers provide a new strategy for synthesizing bispecific antibodies with unique pharmacological activities for biomedical applications.

BIOCHEMISTRY (2023)

Add to Collection

Article Chemistry, Multidisciplinary

A ribose-functionalized NAD+ with versatile activity for ADP-ribosylation

Elisa N. Stephens, Xiao-Nan Zhang, Albert T. Lam, Jiawei Li, Hua Pei, Stan G. Louie, Clay C. C. Wang, Yong Zhang

Summary: The article presents a novel ribose-functionalized NAD(+) with versatile activities that can serve as a general substrate for poly-ADP-ribose polymerases. The mono- and poly-ADP-ribosylated proteins derived from this molecule can be recognized by specific ADP-ribosylation readers, providing valuable insights into developing new probes for ADP-ribosylation.

CHEMICAL COMMUNICATIONS (2023)

Add to Collection

Article Chemistry, Multidisciplinary

A poly-ADP-ribose polymer-based antibody-drug conjugate

Xiaojing Shi, Xiao-Nan Zhang, Jingwen Chen, Qinqin Cheng, Hua Pei, Stan G. Louie, Yong Zhang

CHEMICAL SCIENCE (2020)

Add to Collection

Article Chemistry, Physical

Phosphine-Catalyzed Direct δ-Carbon Addition of Alkynones to Electron-Deficient Carbonyl-Group-Containing Compounds: Preparation of Conjugated Dienes

Yao-Liang Sun, Xiao-Nan Zhang, Yin Wei, Min Shi

CHEMCATCHEM (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Facile chemoenzymatic synthesis of a novel stable mimic of NAD(+)

Zhefu Dai, Xiao-Nan Zhang, Fariborz Nasertorabi, Qinqin Cheng, Hua Pei, Stan G. Louie, Raymond C. Stevens, Yong Zhang

CHEMICAL SCIENCE (2018)

Add to Collection

No Data Available

© Peeref 2019-2024. All rights reserved.