Review
Chemistry, Organic
Regina Westphal, Eclair Venturini Filho, Fabrizio Medici, Maurizio Benaglia, Sandro J. Greco
Summary: This review summarizes the latest developments in asymmetric domino reactions, with a focus on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, reaction mechanisms, rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included.
SYNTHESIS-STUTTGART
(2022)
Review
Chemistry, Organic
Divyang M. Patel, Paras J. Patel, Hitendra M. Patel
Summary: This Review discusses pioneering advances in catalytic stereoselective multicomponent reactions for the preparation of spiro derivatives, highlighting the stereoselective reactions and catalytic mechanisms used in different reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ken-Loon Choo, Bijan Mirabi, Karl Z. Demmans, Mark Lautens
Summary: Enantioenriched spiro-oxiranes with three contiguous stereocenters were synthesized using a rhodium-catalyzed cascade reaction, enabling the formation of a spirocyclic framework in a single step. Both sp(2)- and sp-hybridized carbon nucleophiles were found to be efficient initiators, yielding products with different functional groups. Derivatization studies demonstrated the synthetic versatility of the products' epoxide and alkyne moieties. DFT calculations were employed to explain spectroscopic discrepancies between solution- and solid-state structures of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Zaneta A. Mala, Mikolaj J. Janicki, Robert W. Gora, Krzysztof A. Konieczny, Rafal Kowalczyk
Summary: Dithiomalonates have been shown to be active nucleophiles in stereoselective additions, with Cinchona squaramides facilitating chirality transfer and mechanochemical approach proving to be effective.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Jia-Lu Zhang, Rui Ma, Huan-Huan Zhao, Peng-Fei Xu
Summary: An efficient and concise strategy has been developed for merging spiro-tetrahydroquinoline with spiro-benzofuranone into a single new skeleton through asymmetric catalytic cascade reactions catalyzed by quinine-derived chiral bifunctional squaramide organocatalysts. The approach demonstrates high yields, excellent diastereoselectivities and enantioselectivities (up to 99% yield, up to >20 : 1 dr, up to >99% ee, 40 examples) under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Tao Wang, Bo Huang, You-Qing Wang
Summary: Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3-methylene isoindolinone and in situ-generated ortho-quinone methide substrates is achieved. This reaction allows the construction of spiro chroman-isoindolinones containing spiro-N,O-heterocycles with high enantioselectivity, with a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Ruslan A. Kovalevsky, Alexander S. Kucherenko, Alexander A. Korlyukov, Sergei G. Zlotin
Summary: This study developed a readily scalable asymmetric synthesis technique for chiral chromone derivatives functionalized at position 2 using a simple C-2-symmetric tertiary amine-squaramide catalyst. The reaction products had high yields, the catalyst could be reused, and catalytic hydrogenation and esterification reactions demonstrated synthetic potential of the developed procedure.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Remi Andres, Qian Wang, Jieping Zhu
Summary: A divergent asymmetric total synthesis of voacafricines A and B, hexacyclic monoterpene indole alkaloids, has been achieved by several key steps, including a catalyst-controlled asymmetric Pictet-Spengler reaction, oxidative cleavage, and intramolecular nucleophilic addition. The synthesis confirmed the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle
Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.
Review
Chemistry, Multidisciplinary
Cheng Niu, Da-Ming Du
Summary: This review highlights the recent advancements in sulfa-Michael addition-triggered cascade reactions for the stereoselective synthesis of sulfur-containing compounds. It discusses various types of reactions, including sulfa-Michael/aldol, sulfa-Michael/Henry, sulfa-Michael/Michael, sulfa-Michael/Mannich and some sulfa-Michael triggered multi-step processes. The review also introduces reaction mechanisms and derivatization experiments.
Article
Chemistry, Physical
Camran Ali, Donna G. Blackmond, Jordi Bures
Summary: Nonlinear effects can be observed in asymmetric catalytic cascade reactions without the involvement of higher order catalyst species or reaction steps involving two catalyst species. This may be due to the disruption of pre-equilibria in reversible steps prior to the final irreversible product formation step.
Article
Chemistry, Physical
Zaneta A. Mala, Mikolaj J. Janicki, Natalia H. Niedzwiecka, Robert W. Gora, Krzysztof A. Konieczny, Rafal Kowalczyk
Summary: The carefully designed cinchona alkaloid-based squaramides successfully controlled the enantioselectivity in the cascade of Sulfa-Michael/intramolecular aldol reactions, forming three contiguous stereocenters. The temperature increase did not affect enantioselectivity or diastereoselectivity, revealing the importance of weak interactions in the formation of the multifunctional tetrahydrothiophenes. The Kohn-Sham Density Functional Theory results suggest that a perfect fit between the electrophile and squaramide via tailored (+)N-H hydrogen bonding and pi-pi stacking interactions is crucial for chirality transfer.
Review
Chemistry, Organic
Anup Biswas, Avisek Ghosh, Rajat Shankhdhar, Indranil Chatterjee
Summary: Chiral analogues of squaramides have proved to be efficient asymmetric catalysts in the synthesis of acyclic and cyclic chiral molecules. By utilizing several bifunctional squaramides as catalysts, a wide range of cyclic molecules bearing multiple functionalities and stereocenters have been successfully synthesized.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Rene S. Bitsch, Nicolaj Inunnguaq Jessen, Karl Anker Jorgensen
Summary: Cycloadditions are important reactions in materials science for constructing polycyclic aromatic and heteroaromatic compounds. Recent developments in organocatalysis have allowed for the control of cycloadditions involving an extended number of pi-electrons. This field, known as higher-order cycloadditions, enables the synthesis of polycyclic carbo- and heteroaromatic compounds in two or three dimensions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Guofeng Li, Wangsheng Sun, Jingyi Li, Fengjing Jia, Liang Hong, Rui Wang
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Applied
Guofeng Li, Liwu Huang, Jiecheng Xu, Wangsheng Sun, Junqiu Xie, Liang Hong, Rui Wang
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Multidisciplinary
Gongming Zhu, Junxian Yang, Guangjun Bao, Ming Zhang, Jing Li, Yiping Li, Wangsheng Sun, Liang Hong, Rui Wang
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Multidisciplinary
Zhenhua Zhang, Wangsheng Sun, Gongming Zhu, Junxian Yang, Ming Zhang, Liang Hong, Rui Wang
CHEMICAL COMMUNICATIONS
(2016)
Review
Chemistry, Multidisciplinary
Liang Hong, Wangsheng Sun, Dongxu Yang, Guofeng Li, Rui Wang
Review
Chemistry, Organic
Wangsheng Sun, Guofeng Li, Liang Hong, Rui Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Gongming Zhu, Guangjun Bao, Yiping Li, Junxian Yang, Wangsheng Sun, Jing Li, Liang Hong, Rui Wang
Article
Cell Biology
Ying Gao, Yajun Liu, Liang Hong, Zuolong Yang, Xinran Cai, Xiaoyun Chen, Yuanyuan Fu, Yujie Lin, Weijie Wen, Sitong Li, Xingguo Liu, Heqing Huang, Andreas Vogt, Peiqing Liu, Xiao-Ming Yin, Min Li
CELL DEATH & DISEASE
(2016)
Article
Chemistry, Physical
Ming Zhang, Wangsheng Sun, Gongming Zhu, Guangjun Bao, Bangzhi Zhang, Liang Hong, Min Li, Rui Wang
Article
Chemistry, Multidisciplinary
Chongyang Wu, Huy N. Hoang, Ligong Liu, David P. Fairlie
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Chongyang Wu, Hongyue Zhang, Nan Kong, Bihan Wu, Xinhui Lin, Huaimin Wang
Summary: Chirality correction, asymmetry, ring-chain tautomerism, and hierarchical assemblies are fundamental phenomena in nature that affect the functions of proteins and other supermolecules. A designed alternating D,L peptide was used to recreate and validate the chirality inversion prior to cyclization. The resulting asymmetrical cyclic peptide with a 4-imidazolidinone ring provides a platform to study tautomerism, thermostability, and assembly of nanostructures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chongyang Wu, Huy N. Hoang, Timothy A. Hill, Junxian Lim, W. Mei Kok, Kalyani Akondi, Ligong Liu, David P. Fairlie
Summary: This study shows that an alpha helical turn can be replicated in a cyclic pentapeptide by correctly joining the sidechains of the first and fifth amino acids. Structural studies using CD, NMR, and in silico methods explain how N-methylation at non-hydrogen bond positions disrupts helicity, while ester bonds can maintain helicity and enhance cell uptake.
CHEMICAL COMMUNICATIONS
(2022)
Correction
Chemistry, Multidisciplinary
Huy N. Hoang, Timothy A. Hill, Gloria Ruiz-Gomez, Frederik Diness, Jody M. Mason, Chongyang Wu, Giovanni Abbenante, Nicholas E. Shepherd, David P. Fairlie
Article
Chemistry, Multidisciplinary
Huy N. Hoang, Timothy A. Hill, Gloria Ruiz-Gomez, Frederik Diness, Jody M. Mason, Chongyang Wu, Giovanni Abbenante, Nicholas E. Shepherd, David P. Fairlie
Article
Chemistry, Multidisciplinary
Huy N. Hoang, Chongyang Wu, Renee L. Beyer, Timothy A. Hill, David P. Fairlie
AUSTRALIAN JOURNAL OF CHEMISTRY
(2017)
