Article
Chemistry, Organic
Daniel P. Schwinger, Thomas Pickl, Thorsten Bach
Summary: Cyclohept-1-ene-1-carbaldehyde undergoes photoinduced E & RARR; Z isomerization at & lambda; =350 nm. The ring strain facilitates various reactions, including Diels-Alder cycloadditions, [3 + 2] cycloadditions, and enereactions. The products obtained are trans-fusedat the cycloheptane core and yield up to 82%. Single crystal X-ray analyses confirm the structure and relative configuration. In the presence of BF3 and 2,3-dimethylbuta-1,3-diene, cyclohept-1-ene-1-carbaldehyde undergoes a stereoselective rearrangement to form a tricyclic ketone (87%).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yuan-He Li, Su-Lei Zhang, Yong Lu, Bo Xiao, Tian-Yu Sun, Qian-Qian Xu, Jia-Hua Chen, Zhen Yang
Summary: A highly enantioselective catalytic system for exo-Diels-Alder reactions was developed using bispyrrolidine diboronates(BPDB). Activated by various Lewis or Bronsted acids, BPDB can catalyze highly stereoselective asymmetric exo-Diels-Alder reactions. The catalyst can also distinguish between different binding sites to achieve highly regioselective reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Nan-Fang Mo, Ying Zhang, Zheng-Hui Guan
Summary: An asymmetric organocatalyzed three-component Povarov reaction has been developed to construct azaspirocycles. A chiral phosphoric acid catalyst with a unique structure was highly efficient in the reaction, leading to a wide range of azaspirocycles in high yields and excellent enantioselectivities. This reaction has expanded the scope of the traditional Povarov reaction.
Review
Chemistry, Applied
Maxim G. Vinogradov, Olga V. Turova, Sergei G. Zlotin
Summary: This review retrospectively considers the pivotal achievements and recent advances in catalytic asymmetric aza-DAR reported up to 2020, showcasing their potency for enantioselective synthesis of useful chiral piperidine, quinoline, pyridazine, oxazine, and oxadiazine derivatives. The data are systematized based on key electron transfer modes and attainable heterocyclic products, with significant attention to activation strategies and plausible reaction pathways over stereoselective cyclization processes. The review contains 310 references and 122 synthetic schemes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Xu-Ge Si, Shi-Xiong Feng, Zhuo-Yan Wang, Xiaoyu Chen, Meng-Meng Xu, Yu-Zhen Zhang, Jun-Xiong He, Limin Yang, Quan Cai
Summary: Here, we demonstrate that the combination of Birch reduction and catalytic asymmetric Diels-Alder reaction is a powerful approach for the synthesis of diverse cis-decalin scaffolds. By utilizing a modified chiral bis(oxazoline) ligand/Cu-II complex, we efficiently generated a wide range of polysubstituted cis-decalin scaffolds. Mechanistic studies revealed the role of 1,3-cyclohexadienes as key intermediates and the origins of stereoselectivities in the Diels-Alder reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Qi Xue, Ren Wang, Wen-Yu Zhang, Fang-Fang Shen, Yang Li, Qing Sun, Jin-Heng Li
Summary: A new palladium-catalyzed multicomponent dearomatization of arylamines with CO and propargylic acetates for the synthesis of bridged polycyclic lactams is reported. This method enables double annulation at the ipso and para positions of the amino group, leading to the formation of four new bonds, including three C-C bonds and one C-N bond. DFT calculations and experimental studies suggest that the efficient formation of the allenecarboxanilide intermediate is crucial for the dearomative transformation.
Article
Chemistry, Multidisciplinary
Yang Lu, Meng-Meng Xu, Zhi-Mao Zhang, Junliang Zhang, Quan Cai
Summary: The study presented a copper-catalyzed asymmetric IEDDA reaction for the synthesis of six-membered carbocycles, leading to the successful asymmetric total syntheses of cephanolides A and B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Lenka Pallova, Laura Abella, Marion Jean, Nicolas Vanthuyne, Cecile Barthes, Laure Vendier, Jochen Autschbach, Jeanne Crassous, Stephanie Bastin, Vincent Cesar
Summary: The first efficient chiral helicene-NHC gold(I) complexes for enantioselective catalysis have been synthesized. Their structural and stereochemical characterization confirms their potential in asymmetric catalysis, demonstrated by the benchmark cycloisomerization reaction with high enantiomeric excess.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Jie Ouyang, Rajat Maji, Markus Leutzsch, Benjamin Mitschke, Benjamin List
Summary: Here, we report the design of a highly enantioselective, catalytic (4 + 3) cycloaddition reaction enabled by strong and confined IDPi Lewis acids. This reaction allows the synthesis of novel compounds with multiple stereocenters from gem-dialkyl 2-indolylalcohols and dienolsilanes. The method exhibits broad substrate scope and versatile downstream chemical modifications. Density functional theory-supported mechanistic studies reveal the significance of the in-situ generated silylium species in an overall concerted yet asynchronous cycloaddition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
David J. P. Kornfilt, Brian T. T. Chamberlain, Isabelle Chataigner, Riccardo Spezia, Florence F. F. Wagner
Summary: This manuscript describes the use of HFIP as a unique solvent that allows for the large-scale preparation of BRD4780, a small molecule capable of selectively clearing mutant MUC1-fs protein in mucin kidney disease models. The key Diels-Alder reaction proceeds with >20:1 endo diastereoselectivity in the presence of HFIP. This breakthrough provides a new approach for the synthesis and further studies of BRD4780.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Masao Ohashi, Dan Tan, Jiayan Lu, Cooper S. Jamieson, Daiki Kanayama, Jiahai Zhou, K. N. Houk, Yi Tang
Summary: The synthesis of cis-decalin structures using [4 + 2] cycloaddition with high stereoselectivity is challenging. In this study, we investigated the biosynthetic pathway of the fungal natural product fischerin (1) and identified a novel pericyclase, FinI, which catalyzes this reaction. The cocrystal structure of FinI, a predicted O-methyltransferase, with the product and SAM provides valuable insights into the natural formation of cis-decalin.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Tibor Penaska, Viktoria Modrocka, Klara Stankovianska, Maria Meciarova, Erik Rakovsky, Radovan Sebesta
Summary: This study achieves enantioselective and diastereoselective synthesis of densely substituted chiral pyran derivatives by using amino-thiourea or quinine organocatalyst under ball-milling conditions. Liquid-assisted grinding proves to be a highly efficient means of obtaining pyrans in high yield, with high enantiomeric purities and short reaction times.
Article
Biochemistry & Molecular Biology
Ewa Dresler, Aneta Wroblewska, Radomir Jasinski
Summary: The molecular mechanism of the Diels-Alder reaction depends on the reaction conditions and solvent polarity, with possible pathways including one-step polar mechanisms and stepwise mechanisms involving zwitterionic or heterocyclic intermediates.
Review
Chemistry, Organic
Ghanshyam Mali, Amar Nath Singh Chauhan, Kailas Arjun Chavan, Rohan D. Erande
Summary: The class of Double Diels-Alder (DDA) reactions leads to targets succinctly with conceptually novel and streamlined methods. This growing branch of Diels-Alder reactions triggers the streamlined construction of polycyclic and macrocyclic architectures. The emphasis is on the synthesis of various structural classes based on the selectivity of the DDA reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Julia O. Strelnikova, Alexander N. Koronatov, Nikolai Rostovskii, Alexander F. Khlebnikov, Olesya Khoroshilova, Mariya A. Kryukova, Mikhail S. Novikov
Summary: The domino reaction catalyzed by Rh-2(Piv)(4) leads to the formation of N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles, providing a direct and flexible access to the desired compounds.
Article
Chemistry, Multidisciplinary
Norito Takenaka, Robindro Singh Sarangthem, Burjor Captain
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2008)
Article
Chemistry, Multidisciplinary
Zhili Peng, Norito Takenaka
Article
Chemistry, Multidisciplinary
Jinshui Chen, Norito Takenaka
CHEMISTRY-A EUROPEAN JOURNAL
(2009)
Review
Chemistry, Organic
Maurice J. Narcis, Norito Takenaka
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2014)
Article
Chemistry, Multidisciplinary
Norito Takenaka, Jinshui Chen, Burjor Captain, Robindro Singh Sarangthem, Appayee Chandrakumar
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2010)
Article
Chemistry, Organic
Maurice J. Narcis, Daniel J. Sprague, Burjor Captain, Norito Takenaka
ORGANIC & BIOMOLECULAR CHEMISTRY
(2012)
Article
Chemistry, Organic
Jinshui Chen, Burjor Captain, Norito Takenaka
Article
Chemistry, Organic
Carlyn Reep, Pierpaolo Morgante, Roberto Peverati, Norito Takenake
Article
Chemistry, Organic
Andreina Aguado, Norito Takenaka
Review
Chemistry, Organic
Carlyn Reep, Shiyu Sun, Norito Takenaka
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Pierpaolo Morgante, Burjor Captain, Christopher D. Chouinard, Roberto Peverati, Norito Takenaka
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Changgong Xu, Phillip Nader, Jonathan Xavier, Burjor Captain, Norito Takenaka
Summary: Helicene-derived 2,2'-bipyridine N-monoxide was used as a Lewis base catalyst for the enantioselective propargylation of non-activated acylhydrazones, showing moderate-to-good reactivity and enantioselectivity for a range of acylhydrazones. This is the first example of asymmetric propargylation of non-activated acylhydrazones using this catalyst.
Article
Chemistry, Organic
Norito Takenaka, Robindro Singh Sarangthem, Sreehari Kumar Seerla
Article
Chemistry, Multidisciplinary
Norito Takenaka, Joshua P. Abell, Hisashi Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2007)