Article
Chemistry, Organic
Lorenzo Serusi, Laura Palombi, Giovanni Pierri, Antonia Di Mola, Antonio Massa
Summary: The asymmetric synthesis of novel 3-substitued isoindolinones was achieved using the asymmetric nitro-Mannich reaction and the in situ cyclization reaction. High enantioselectivities and yields were obtained in the presence of a neutral bifunctional organocatalyst. The investigation of the reactivity of the obtained products also revealed the potential for further functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pritam Roy, Anugam V. Krishna, Dhevalapally B. Ramachary
Summary: Biologically important 4-alkylsyncarpic acids were synthesized through a one-pot organocatalytic reaction, and their synthetic applications were demonstrated. Formal total synthesis of important derivatives was achieved starting from 4-alkylsyncarpic acids. The importance of C-alkylated products was further showcased.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
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, Organic
Ryan R. G. Barrett, Donald A. Campbell, James L. Gleason
Summary: Ethyl diazepane carboxylate catalyzes the oxy-Cope rearrangement of 4-hydroxy- and 4-alkoxy-1,5-hexadiene-2carboxaldehydes via iminium ion activation, leading to cyclopentane-containing products through intramolecular Michael reaction. The reaction is applicable to various substrates, including cyclic and acyclic ones, and shows tolerance towards vinyl substituent substitution. Substrates with cycloalkane framework undergo net ring expansion/cyclopentannulation with high stereocontrol through chairlike transition states. This reaction expands iminium organocatalysis to the oxy-Cope rearrangement within a complexity-generating cascade transformation.
Review
Chemistry, Multidisciplinary
Yin Xu, Tong-Yi Zhai, Zhou Xu, Long-Wu Ye
Summary: Desymmetrization is a practical and efficient strategy in synthetic chemistry for assembling valuable molecular complexity. Organocatalysis has become a powerful tool in asymmetric catalysis, and recent progress has been made in combining organocatalysis with desymmetrization.
TRENDS IN CHEMISTRY
(2022)
Review
Chemistry, Organic
Yongchao Wang, Angel A. Cobo, Annaliese K. Franz
Summary: This review summarizes recent advances in the enantioselective construction of spirooxindoles using chiral phosphoric acids, amines, and bifunctional thiourea/squaramides as catalysts.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Jiaming Zou, Lei Xu, Yurong Tang, Wentao Wang, Yunfei Cai
Summary: The asymmetric synthesis of bridged tetrahydrobenzo[b]azepine and oxepine derivatives has been achieved through chiral Bri nsted acid catalyzed asymmetric aza-Piancatelli rearrangement/Michael addition sequence. The reaction proceeds under mild reaction conditions to afford the final bridged cyclic products in good yields with excellent enantio- and diastereoselectivities.
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, Organic
Rayhan G. Biswas, Sumit K. Ray, Rajshekhar A. Unhale, Vinod K. Singh
Summary: A bifunctional urea catalyzed cascade reaction of 5-alkenyl thiazolones and monofluorinated beta-diketones, derived from quinine, has been developed, yielding fluorine containing 4-acyloxy thiazoles with high yields and good diastereo- and excellent enantioselectivities. Synthetic transformations, including the synthesis of 4-hydroxy thiazoles, have been successfully demonstrated.
Article
Chemistry, Applied
Jen-Yu Kuan, I-Ting Chen, Hsuan Lin, Jeng-Liang Han
Summary: We have developed a substrate-dependent, regio- and stereocontrolled diversity-oriented organocatalytic vinylogous Michael addition/cyclization cascade of 2-alkylidene indane-1,3-diones with enals, using secondary amines as the catalyst. This method allows for the selective synthesis of spiroindane-1,3-diones, tetrahydrofluoren-9-one derivatives, and benzofused oxabicyclo[3.3.1]nonanes. Plausible catalytic pathways have been proposed, and DFT calculations have clarified the mechanisms involved.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Hui Zhou, Yi-Feng Zhang, Wei Chen, Wen-Zhen Zhang, Xiao-Bing Lu
Summary: The first cascade reaction between CO2-sourced cyclic carbonates and hydroperoxides is reported using an effective commercially available organocatalyst, providing a sustainable method for the formation of peroxy-substituted cyclic carbonates.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Moritz Sinast, Birgit Claasen, Yannick Stoeckl, Andreas Greulich, Anna Zens, Angelika Baro, Sabine Laschat
Summary: A new approach has been developed for the synthesis of key structures of the clifednamide family with high yield and enantiomeric excess, offering a potential pathway for key intermediates in the clifednamide biosynthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Pratibha Sharma, Raakhi Gupta, Raj K. Bansal
Summary: The article reviews the literature on asymmetric aza-MR of amines and amides catalyzed by organocatalysts in the past 10 years. Studies show that both types of organocatalysts, whether through non-covalent interactions or through covalent bond formation, play important roles in this reaction.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xin Qin, Jinhai Zhang, Zhan-Yong Wang, Yimei Song, Yixiao Yang, Wenhai Zhang, Hongxin Liu
Summary: In this study, a aldol/Michael cascade reaction on the beta,gamma-positions of alpha,beta-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates exhibited high regio- and diastereoselectivities and yielded moderate to good results (32 examples). Control experiments showed that the hydrogen of the amide played a key role.
Article
Chemistry, Applied
Laiyu An, Linghong Chen, Hongzhou Yang, Ling Ye, Hongjun Yang, Xinying Li, Zhigang Zhao, Xuefeng Li
Summary: A convenient and functionalized vinylogous nucleophile has been used to synthesize bridged bicyclic compounds via cascade Michael/Henry reaction. The reaction showed high reactivity without the need for a catalyst under mild conditions. Various structurally distinctive bicyclo[3.2.1]octanes were obtained in isolated yields of 40-96% with excellent diastereoselectivities (& GE;10:1 dr). The gram-scale synthesis was also demonstrated.
ADVANCED SYNTHESIS & CATALYSIS
(2023)