Article
Chemistry, Organic
Shi-Jie Zhu, Zhi-Feng Hao, Ya Pan, Ying Zhou, Xiong-Li Liu, Ming Zhang, Chuan-Wen Lei
Summary: In this study, a stepwise enantioselective formal (3 + 2) cyclocondensation reaction was successfully accomplished, leading to the synthesis of spiro-fused pentacyclic spirooxindoles. The reaction showed good overall yields, excellent dr, and high ee values.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shi-Jie Zhu, Zhi-Feng Hao, Ya Pan, Ying Zhou, Xiong-Li Liu, Ming Zhang, Chuan-Wen Lei
Summary: The first enantioselective formal (3 + 2) cyclocondensation involving alpha,fi-unsaturated pyrazoleamides as 3-carbon partners was successfully achieved in a stepwise fashion. The protocol led to the synthesis of spiro-fused pentacyclic spirooxindoles with good overall yields, excellent diastereomeric ratios, and high enantiomeric excess values.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Andrea Guerrero-Corella, Miguel A. Valle-Amores, Alberto Fraile, Jose Aleman
Summary: An asymmetric organocatalytic aza-Michael addition reaction of ketimines to nitroolefins is described, utilizing 2-hydroxybenzophenone imine to improve the enantioselective addition of N-centered nucleophiles to nitroalkenes. The versatility of the process is demonstrated under both batch and flow conditions, resulting in the synthesis of a wide variety of nitroamine derivatives with excellent yields and enantioselectivities. Additionally, this methodology was successfully applied to the formal synthesis of VNI, a drug-like scaffold for the treatment of Chagas disease.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Connor Kabes, Reagan Lucas, Jack Gunn, John Gladysz
Summary: The lipophilic diastereomeric cobalt complexes catalyze enantioselective C-H bond addition reactions with aliphatic tertiary amines. Incorporating different bases into counter anions can lead to highly enantioselective bifunctional catalysts, where salts of nicotinates and related compounds have been found effective. The 6-aminonicotinate salt gives the best results among the tested bases.
Review
Chemistry, Organic
Girija S. Singh
Summary: Asymmetric organic synthesis is crucial in drug development, with many functional group transformation reactions seeing significant progress under green conditions.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuntong Li, Wen-Qiang Wu, Hui Zhu, Qi-Kai Kang, Lun Xu, Hang Shi
Summary: In this study, we report Rh-catalyzed benzylic addition of alkylarenes to Michael acceptors, which involves the activation of the aromatic ring for deprotonation of the unactivated benzylic C-H bond and addition of the resulting carbanion to the α,β-unsaturated double bond. This byproduct-free method provides access to all-carbon quaternary centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Chandan K. Mahato, Sayan Mukherjee, Mrinalkanti Kundu, Virbhadra P. Vallapure, Animesh Pramanik
Summary: This study utilized a new set of organic catalysts for asymmetric Michael reactions in water, achieving high efficiency and yield, offering a new method for green synthesis. The strategy also successfully synthesized an optically active octahydroindole, a key component found in many natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yiqi Ren, Maodi Wang, Qihua Yang, Junfa Zhu
Summary: The development of chiral solid catalysts using unconventional strategies is crucial for efficient heterogeneous asymmetric catalysis. The study presents a chiral solid catalyst, chiral diamine modified Ni/SiO2, for asymmetric Michael addition. The experimental results demonstrate that the peripheral Ni sites in close contact with SiO2 support are likely to be the active sites.
Article
Chemistry, Multidisciplinary
Qingdong Hu, Chang Guo
Summary: The synthesis of structurally diverse multiligated platinum complexes, characterized by X-ray crystallography, opens up new reaction space and enables faster screening. The Pt/Cu dual catalytic system shows new cooperative reactivity, leading to the asymmetric synthesis of valuable functionalized indoles with good yields and excellent enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Yuelin Xu, Fengxi Li, Jinglin Ma, Jiapeng Li, Hanqing Xie, Chunyu Wang, Peng Chen, Lei Wang
Summary: This study reveals a new biocatalytic strategy for the direct synthesis of organophosphorus compounds with C-P bonds. The strategy shows good functional group compatibility and practical operation, with potential broad applications in organic synthesis.
Article
Biochemistry & Molecular Biology
Yvette Lock Toy Ki, Armelle Garcia, Franck Pelissier, Tomasz K. Olszewski, Alicja Babst-Kostecka, Yves-Marie Legrand, Claude Grison
Summary: The Michael addition reaction was studied in the context of sustainability and efficiency through mechanochemistry. Eco-bases, derived from plants, were used as catalysts instead of classical bases, resulting in rapid and efficient reactions with low catalyst loading. The Eco-bases exhibited good recyclability and were effective in various Michael donors and acceptors. This study is significant for the development of mechanochemistry in sustainable chemistry.
Article
Chemistry, Physical
Qihua Yang, Junfa Zhu, Yiqi Ren, Maodi Wang
Summary: In this study, a chiral solid catalyst, chiral diamine modified Ni/SiO2, was prepared for asymmetric Michael addition. The experimental results showed that the chiral diamine modified Ni/SiO2 achieved a higher ee value and turnover frequency compared to chiral Ni complexes. The peripheral Ni sites in close contact with SiO2 support were identified as the active sites, distinct from homogeneous complexes. Continuous flow production of chiral compounds for more than 65 hours was achieved using the solid catalysts in a fixed bed reactor.
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yong-Sin Chen, Ming-Hsuan Huang, Yan-Peng Cheng, Duen-Ren Hou
Summary: In this study, chiral N-substituted 4-pyrimidinones were prepared for the first time through an enantioselective, organocatalytic aza-Michael addition reaction. The optimization of solvents, catalysts, and acceptors resulted in high yields and enantioselectivities.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Hanwei Lu, Hebo Ye, Meilan Zhang, Zimu Liu, Hanxun Zou, Lei You
Summary: Phototriggered click and clip reactions can achieve high spatiotemporal resolution and sustainability in chemical processes, and this study reports a photoswitchable reversible covalent conjugate addition-elimination reaction with a broad scope. By coupling a photochromic dithienylethene switch with Michael acceptors, the reactivity of Michael reactions can be controlled, allowing the dynamic exchange of various nucleophiles. The authors demonstrate the versatile applications of this reaction, including light-mediated surface modification, regulation of amphiphilic assemblies, and creation/degradation of covalent polymers on demand.
NATURE COMMUNICATIONS
(2023)