Article
Chemistry, Organic
Merve Karaoglu, Feray Aydogan, Cigdem Yolacan
Summary: The aldol reaction is a key reaction for synthesizing organic compounds, and some Pro-Phe derivatives show promising catalytic activities in this reaction, especially in water. This catalyst also meets the requirements of green chemistry.
LETTERS IN ORGANIC CHEMISTRY
(2021)
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)
Article
Chemistry, Organic
E. H. Nisala Fernando, Jose Cortes Vazquez, Jacqkis Davis, Weiwei Luo, Vladimir N. Nesterov, Hong Wang
Summary: The formation of enamine from primary arylamines was studied and confirmed, with the necessity of a radical quencher for detection. A direct synthesis of alpha-enaminones from primary arylamines and ketones was developed, and a mechanistic investigation suggested the involvement of an amine radical cation. The reactivity and utility of alpha-enaminones were explored, showing different properties from enamines and advancing understanding in organic chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Pratikkumar Lakhani, Chetan K. Modi
Summary: In this work, a groundbreaking strategy for the synthesis of L-proline chiral scaffold tethered onto the silica matrix was reported. The synthesized catalyst showed excellent activity in an asymmetric aldol reaction with high enantioselectivity. Moreover, the catalyst could be recycled multiple times without any loss of activity.
MOLECULAR CATALYSIS
(2022)
Review
Chemistry, Organic
Zorana Ferjancic, Radomir N. Saicic
Summary: The combination of organocatalytic aldol reaction and reductive amination allows for rapid, stereoselective synthesis of N-heterocycles, which is of great significance for the synthesis of iminosugars and other polyhydroxylated alkaloids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ruslan A. Kovalevsky, Konstantin V. Vasechkin, Alexander S. Kucherenko, Sergei G. Zlotin
Summary: A direct enantioselective synthesis of 2-substituted chromen-4-ones with an amino group at the α-stereogenic center of the heterocycle has been developed. This method is based on Mannich-type asymmetric addition of 3-hydroxychromen-4-one and its analogues to N-protected imines in the presence of the alkaloid dihydrocuprein. α-Stereogenic chromenone amino derivatives were obtained in yields of 81-95% with up to 98% ee. The chiral adducts were then transformed into various enantiomerically enriched chromen-4-one functional derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Veronica Diaz-Juarez, Carlos Ernesto Reyes-Escobedo, Mario Perez-Venegas, Eusebio Juaristi, Salvador Perez-Estrada, Susana Rojas-Lima, Heraclio Lopez-Ruiz
Summary: The (S)-proline-thiourea 1 host-guest complex is reported as an efficient catalyst in the enantioselective aldol reaction of ketones with aldehydes. This complex shows high yields, enantioselectivities, and diastereoselectivities under various conditions, such as at 0 degrees C, in a non-polar solvent like toluene, or under solvent-less conditions.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Axel Leblond, Ines Houari, Yann Beauxis, Karine Leblanc, Erwan Poupon, Mehdi A. Beniddir
Summary: In this study, an unconventional strategy was used to mimic the catalytic conditions of ketosterase, leading to the successful synthesis of nesteretal A and its analogues.
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)
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
Mohammad Hosein Sayahi, Fatemeh Shamkhani, Mohammad Mahdavi, Saeed Bahadorikhalili
Summary: This paper presents an efficient method for the synthesis of 10-methyl-7-aryl-7,12-dihydro-6H,8H-chromeno[4,3-b]pyrano[3,4-e]pyridine-6,8-dione derivatives in water using non-toxic catalyst L-proline. The method avoids the use of any toxic solvent and shows promise for green chemistry practices.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
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, Organic
David Guzman Rios, Miguel A. Romero, Jose A. Gonzalez-Delgado, Jesus F. Arteaga, Uwe Pischel
Summary: The [Ru(bpy)2(Nor)2]2+ complex is an efficient catalyst for the aldol reaction of acetone with activated benzaldehydes in a buffered aqueous solution. The role of the metal as an activator for nornicotine organocatalyst ligands enhances catalytic activity by about 4.5 times compared to free nornicotine. The study provides insights into the synergistic effect of organic catalysts and metals.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhi-Hong Du, Meng Yuan, Bao-Xiu Tao, Wen-Juan Qin, Xiang-Ming Liang, Yu-Yan Li, Hang Lin, Lian-Chun Zhang, Chao-Shan Da
Summary: This study demonstrates that a tert-leucine-derived organocatalyst can efficiently catalyze the asymmetric cross-aldol reaction of glyoxylate and alkyl aldehydes at room temperature with high yield and enantioselectivity. The tert-leucine with a large side group is essential for the high enantioselectivity. Additionally, the reaction shows potential for the eco-friendly chemical production of the pharmaceutical intermediate (R)-pantolactone with high yield and enantiopurity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
A. Uyanik, O. Sahin, E. Akceylan, S. Eymur, I. Uyanik, M. Yilmaz
Summary: A new organocatalyst was synthesized and studied for its catalytic performance in the direct asymmetric aldol reactions. The addition of water was found to have a significant effect on the enantioselectivities, leading to high selectivity in the reaction between cyclohexanone and 4-fluorobenzaldehyde.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2022)