Article
Chemistry, Applied
Byungjun Kim, Sukwoo Lee, Sarah Yunmi Lee
Summary: In this study, a new method was reported to successfully promote the catalytic asymmetric Diels-Alder reactions using a chiral catalyst in conjunction with a chiral isothiourea catalyst or a Bronsted acid, resulting in the synthesis of densely functionalized cyclohexenes with multiple stereocenters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Applied
Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi
Summary: Pyrazoleamides have gained attention as reactive and practical surrogates in asymmetric catalysis, particularly in a variety of metal- and organocatalytic transformations. Their relevance has extended to photoredox catalysis and challenging stereoselective bond-forming reactions in recent years.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Ingolf Harden, Frank Neese, Giovanni Bistoni
Summary: The formation of Bronsted acid aggregates in asymmetric organocatalytic reactions has a significant impact on the stereo-controlling factors of the transformations. This study uses high-level quantum mechanical calculations to investigate the influence of catalyst structure and reaction conditions on the spontaneity of the aggregation process, shedding light on its importance.
Article
Chemistry, Multidisciplinary
Ingolf Harden, Frank Neese, Giovanni Bistoni
Summary: This study investigates the aggregation process of chiral organocatalysts derived from phosphoric acids using high-level quantum mechanical calculations. The results show that the formation of catalyst dimers is possible and the aggregation process can significantly affect the stereo-controlling factors, reaction kinetics, and selectivity of the transformations.
Article
Nanoscience & Nanotechnology
Miguel Sanchez-Fuente, Alberto Lopez-Magano, Alicia Moya, Ruben Mas-Balleste
Summary: Condensation of BINAPO-(PhCHO)(2) and 1,3,5-tris(4-aminophenyl)benzene(TAPB) leads to a new imine-based chiral organic material (COM) that can be post-functionalized through reductive transformation of imine linkers to amines. Although the imine-based material is not stable enough to be used as a heterogeneous catalyst, the reduced amine-linked framework can be efficiently utilized in asymmetric allylation of various aromatic aldehydes. The obtained yields and enantiomeric excesses are comparable to those observed for the molecular BINAP oxide catalyst, with the added advantage of recyclability offered by the amine-based material.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Feng-Tao Sheng, Shuang Yang, Shu-Fang Wu, Yu-Chen Zhang, Feng Shi
Summary: A new strategy for the enantioselective synthesis of axially chiral 3,3'-bisindoles was developed by directly coupling two indole rings using the C3-umpolung reactivity of 2-indolylmethanols. The synthesized compounds can be further modified to create axially chiral 3,3'-bisindole-based organocatalysts for asymmetric catalysis.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Taiki Mori, Ryuichi Nishiyori, Sao Sumida, Yasuaki Furuya, Seiji Shirakawa
Summary: The development of efficient CO2 utilization reactions has attracted significant attention, but the research on catalytic enantioselective CO2 utilization for fine chemicals is still limited. There have been excellent methods reported using chiral metal complex catalysts, as well as organocatalyzed approaches. This review focuses on recent advances in catalytic enantioselective CO2 utilization reactions using chiral organocatalysts and provides a forecast for future research.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Isaac G. Sonsona, Andrea Vicenzi, Marco Guidotti, Giorgiana Denisa Bisag, Mariafrancesca Fochi, Raquel P. Herrera, Luca Bernardi
Summary: The study demonstrates the improved selectivity of an asymmetric aldol reaction by replacing part of the catalyst, and identifies the most suitable reaction conditions. However, these conditions seem to be limited to oxindoles bearing a 3-substituent of funapide.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Emilien Le Saux, Dengke Ma, Pablo Bonilla, Catherine M. Holden, Danilo Lustosa, Paolo Melchiorre
Summary: A general iminium ion-based catalytic method for enantioselective conjugate addition of carbon-centered radicals to aliphatic and aromatic enals is reported in this study. The process uses an organic photoredox catalyst and a chiral amine catalyst to achieve consistently high levels of stereoselectivity. This catalytic platform is demonstrated to have broad applicability in intercepting various radicals, including non-stabilized primary ones that are typically challenging to engage in asymmetric processes. Additionally, the system can be used to develop organocatalytic cascade reactions, producing stereochemically dense chiral products in one step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Mariia Babkova, Rene Wilhelm
Summary: In this study, a series of new multifunctional organocatalysts were prepared and evaluated for the asymmetric aldol reaction of acetone and aromatic aldehydes. Several of the catalysts exhibited high catalytic activity and selectivity. The combination of camphor-based moiety and proline-based unit was found to be crucial for the performance of the catalysts.
Article
Chemistry, Applied
Armando Carlone, Luca Bernardi, Peter McCormack, Tony Warr, Srinivas Oruganti, Christopher J. Cobley
Summary: The scale up development of an innovative synthetic process to pregabalin relies on continuous chemistry and asymmetric organocatalysis, with successful optimization of reaction conditions and organocatalyst recycle.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Stuart C. D. Kennington, Saul F. Teloxa, Miguel Mellado-Hidalgo, Oriol Galeote, Sabrina Puddu, Marina Bellido, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes was reported. The reaction gives high yields of O-TIPS-protected anti-aldol adducts with remarkable stereocontrol and atom economy. The removal of the achiral scaffold provides enantiomerically pure intermediates with synthetic interest for producing anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives, with theoretical calculations explaining the observed high stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Leon Hoppmann, Olga Garcia Mancheno
Summary: The review focuses on the organocatalytic applications of silyl-dienolates in asymmetric vinylogous C-C bond formations, highlighting their high regioselectivities and catalytic characteristics.
Article
Chemistry, Applied
Maxim Smirnov, Alexander S. Kucherenko, Ilya D. Gridnev, Alexander A. Korlyukov, Sergei G. Zlotin
Summary: Biomass derived gamma-pyrone-2-carbaldehydes were used as a robust platform for carrying out organocatalytic asymmetric cross-aldol reactions with high yield and excellent stereoinduction. The origins of efficient stereoinduction were revealed by quantum-chemical calculations, and the products were successfully converted to synthetically useful chiral compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Raghunath Chowdhury, Akhil K. Dubey, Mario Waser
Summary: Asymmetric decarboxylative aldol reactions of MAHTs, MAHOs, and beta-ketoacids with different carbonyl compounds are valuable transformations for the direct synthesis of enantio-enriched beta-hydroxy esters and ketones. Organocatalysis and metal catalysis are the leading strategies for carrying out these reactions in recent progress.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Alexander S. Kucherenko, Alexey A. Kostenko, Galina M. Zhdankina, Olga Yu. Kuznetsova, Sergei G. Zlotin
Article
Chemistry, Organic
Vladimir A. Ogurtsov, Pavel V. Dorovatovskii, Yan V. Zubavichus, Victor N. Khrustalev, Artem N. Fakhrutdinov, Sergei G. Zlotin, Oleg A. Rakitin
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Multidisciplinary
Ilya V. Kuchurov, Svetlana S. Arabadzhi, Mikhail N. Zharkov, Leonid L. Fershtat, Sergei G. Zlotin
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2018)
Review
Chemistry, Organic
Valerii A. Pavlov, Sergey G. Zlotin
CURRENT ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Sergei V. Kochetkov, Alexander S. Kucherenko, Sergei G. Zlotin
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Organic
Alexey A. Kostenko, Alexander S. Kucherenko, Sergei G. Zlotin
Article
Chemistry, Organic
Rinat S. Tukhvatshin, Alexander S. Kucherenko, Yulia V. Nelyubina, Sergei G. Zlotin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
N. V. Obruchnikova, R. A. Novikov, S. G. Zlotin, P. V. Dorovatovskii, V. N. Khrustalev, O. A. Rakitin
RUSSIAN CHEMICAL BULLETIN
(2018)
Article
Chemistry, Organic
Alexander S. Kucherenko, Alexey A. Kostenko, Andrey N. Komogortsev, Boris V. Lichitsky, Michael Yu. Fedotov, Sergei G. Zlotin
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Review
Multidisciplinary Sciences
Valerii A. Pavlov, Yaroslav V. Shushenachev, Sergey G. Zlotin
Article
Chemistry, Multidisciplinary
K. A. Bykova, A. A. Kostenko, A. S. Kucherenko, S. G. Zlotin
RUSSIAN CHEMICAL BULLETIN
(2019)
Article
Chemistry, Multidisciplinary
Mikhail N. Zharkov, Svetlana S. Arabadzhi, Ilya V. Kuchurov, Sergei G. Zlotin
REACTION CHEMISTRY & ENGINEERING
(2019)
Review
Chemistry, Organic
Maxim G. Vinogradov, Olga V. Turova, Sergei G. Zlotin
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Alexey A. Kostenko, Alexander S. Kucherenko, Andrey N. Komogortsev, Boris V. Lichitsky, Sergei G. Zlotin
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
