Article
Chemistry, Organic
Cong-Cong Zhang, Li-Jun Chen, Bao-Chun Shen, Hui-Ding Xie, Wei Li, Zhong-Wen Sun
Summary: This study demonstrated a concise and efficient method for enantioselective synthesis of beta-keto propargylamines via chiral phosphoric acid-catalyzed asymmetric Mannich reaction. The method provides a wide scope of products with high yields and generally high enantioselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shuxuan Liu, Hui Qian, Tianyu Zhang, Hongling Xie, Zhengyu Han, Wengang Guo, Hai Huang, Jianwei Sun
Summary: This study presents a new method for accessing cyclopropanes embedded in a polycyclic bridged architecture through a mild intermolecular convergent process. Unlike conventional approaches, this protocol does not require highly active carbenoid intermediates or strong conditions. The key cyclopropane ring is formed between the well-positioned nucleophile and electrophile in the adduct, showing a new reactivity of the versatile isobenzopyryliums.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xianghong Xu, Lingzi Peng, Xihao Chang, Chang Guo
Summary: The highly enantioselective O-propargylation catalyzed by combining a phosphine-nickel complex and an axially chiral sodium dicarboxylate offers a mild reaction conditions, broad substrate scope, and excellent functional group tolerance, leading to efficient synthesis of an array of enantioenriched compounds. The mechanistic studies support the role of the chiral carboxylate as a counterion for nickel catalysis, enabling the discovery of highly stereoselective transformations, showcasing its power in the asymmetric total synthesis of potent firefly luciferase inhibitors and (S)-dihydroyashabushiketol.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Brijesh Patel, Shilpa Dabas, Parth Patel, Saravanan Subramanian
Summary: One of the fundamental aims in catalysis research is to understand the factors that contribute to the superior performance of a certain scaffold as a catalyst. In this study, a simple and scalable electrostatically tuned phenol (ETP) was used as an organic catalyst for the transfer hydrogenation of N-arenes. The charged environment plays a crucial role in the catalytic transformation, and the biomimetic catalyst showed promising catalytic activity.
Article
Chemistry, Organic
Gao-feng Yang, Guang-xun Li, Jin Huang, Ding-qiang Fu, Xiao-kang Nie, Xin Cui, Jin-zhong Zhao, Zhuo Tang
Summary: An unexpected tandem cyclization/transfer hydrogenation reaction was developed for the synthesis of chiral 2,3-disubstituted 1,5-benzodiazepines. The reaction, catalyzed by chiral phosphoric acid, exhibited moderate yields, good selectivities, and high enantiomeric ratios, providing a new method for the synthesis of this class of compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Florian Sachse, Christoph Schneider
Summary: A cooperative, one-pot approach has been developed for the in situ generation and subsequent cycloaddition of thioaldehydes and ortho-quinone methides under UV-A light and Brønsted acid catalysis, providing direct access to benzo[e][1,3]oxathiines in good to excellent yields and diastereoselectivity. Both electron-rich and electron-poor thioaldehydes can easily react with a wide range of ortho-quinone methides at ambient temperature in a short reaction time, producing a variety of S,O-heterocycles.
Article
Chemistry, Multidisciplinary
Zebediah C. Girvin, Laura F. Cotter, Hyung Yoon, Steven J. Chapman, James M. Mayer, Tehshik P. Yoon, Scott J. Miller
Summary: High selectivity in photochemical reactions can be achieved by controlling the transition state.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jiadong Tang, Can Chen, Tao Hong, Zibin Zhang, Chunsong Xie, Shijun Li
Summary: Supramolecular asymmetric catalysis is an important field that combines supramolecular chemistry and asymmetric catalysis. By utilizing crown ether-based host-guest chemistry and chiral phosphoric acid, the catalytic reaction can be regulated, leading to improved yield and enantioselectivity of the catalyst.
Review
Chemistry, Organic
Caroline Dorsch, Christoph Schneider
Summary: This review summarizes recent developments in the area of enantioselective cycloadditions catalyzed by Bronsted acids. Through a straightforward transformation, complex polycyclic heterocyclic compounds can be obtained with high yields and excellent stereocontrol. The enantioselectivity of the reaction is controlled by chiral Bronsted acids.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Gaukhar Khassenova, Olga Garcia Mancheno
Summary: The Lewis base-Brønsted acid co-catalyzed Morita-Baylis-Hillman reaction of cyclic sulfamidate imines with acrylate-type Michael acceptors using equimolecular amounts of DABCO and acetic acid proved highly efficient and tolerated a wide range of substrates. The reaction provides a straightforward access to sulfamidates bearing alpha,beta-unsaturated chains, allowing for further functionalization of the products. The robustness and applicability of the method was demonstrated by performing a gram scale reaction and further functionalization of the MBH-adducts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Neeraj Kumar Mishra, Amitava Rakshit, Kyeongwon Moon, Pargat Singh, In Su Kim
Summary: The synthesis and functionalization of privileged nitrogen heterocycles play a central role in drug discovery and material science. Tandem C-H functionalization and intramolecular annulation have gained significant attention for their ability to expedite the construction of heteroaromatic frameworks. While there has been progress in the [3 + 2] dipolar cycloaddition of azomethine imines with pi-unsaturated compounds, the combination of catalytic C-H functionalization and intramolecular cyclization using azomethine imines as both directing groups and dipolar units remains less explored.
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Jorge Escorihuela, Santos Fustero
Summary: The chemistry of fluorinated compounds has grown significantly in recent decades due to the diverse properties they possess. Among them, fluorinated chiral imines, especially the Ellman's imines, are crucial in the synthesis of enantioenriched carbocycles and heterocycles with exceptional biological and synthetic properties. This personal account highlights the important findings of our research group in the past two decades, focusing on asymmetric tandem reactions, particularly the intramolecular aza-Michael reaction, diversity oriented synthesis, asymmetric tandem reactions involving a p-tolylsulfinyl group, cycloaddition processes, and the use of fluorinated chiral N-sulfinyl imines and their derivatives as starting materials for enyne compounds in Pauson-Khand reactions, [2+2+2]-cycloadditions, and metathesis reactions.
Article
Chemistry, Multidisciplinary
Qian Rao, Yin Zhang, Yin-Ping Liu, Bo Jiang, Xiang Wang, Tu Shu-Jiang, Wen-Juan Hao
Summary: A novel gold(I)/Bronsted acid relay catalysis enables the activation of azofuran and induces annulative rearrangement from 3-yne-1,2-diols and aryldiazonium tetrafluoroborates, resulting in the formation of furan-2-yl-substituted pyrrol-2-ones bearing a quaternary carbon center with good yields. Substituting aryldiazonium tetrafluoroborate with azofuran yields structurally identical but substituent-diverse furan-2-yl-containing pyrrol-2-ones with good yields, providing support for the crucial role of azofuran activation and annulative rearrangement by gold/Bronsted acid relay catalysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Cong-Hui Gao, Lei Yu, Xin-Yue Wu, Hong-Lin Wan, Wei Tan, Feng Shi
Summary: A tandem cyclization/addition reaction of 1,4-enediones with 2-naphthols was catalyzed by Bronsted acid, leading to the synthesis of a series of 2-furylmethylnaphthalenes with high yields (up to 98%). Control experiments provided insights into the possible reaction pathway and activation mode, contributing to the understanding of Bronsted acid catalysis and tandem reactions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jeremy T. Maddigan-Wyatt, Jing Cao, Jhi Ametovski, Joel F. Hooper, David W. Lupton
Summary: Here, an enantioselective catalytic annulation of electron-poor allenes with aminocrotonates is reported. The reaction proceeds via umpolung gamma-amination and beta-umpolung intramolecular conjugate addition. The reaction provides ready access to chiral compounds with high yields and high enantiomeric ratios, and an assisted tandem-catalytic variant is also proposed.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
