Article
Chemistry, Applied
Yujiro Hayashi, Masashi Tomikawa, Naoki Mori
Summary: The asymmetric cross-aldol reaction is a synthetically relevant reaction. The reactivity and stereoselectivity of different catalysts were compared for the reaction, and it was found that the proper selection of catalysts can lead to the synthesis of chiral building blocks with high diastereoselectivities and enantioselectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Ryoga Hikawa, Mio Shimogaki, Taichi Kano
Summary: Novel threonine-derived amino sulfonamide organocatalysts were developed and successfully applied to asymmetric aldol reactions. The reactions produced anti-aldol adducts with high diastereo- and enantioselectivity when catalyzed by threonine-derived tosylamide, and syn-aldol adducts were obtained when using threonine-derived triflamide catalyst in reactions between alpha-siloxyacetone and aromatic aldehydes. In both cases, a significant improvement in diastereoselectivity was observed compared to threonine-derived carboxylic acid catalyst.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Jae Ho Shim, Ji Yeon Lee, Hyeon Soo Kim, Deok-Chan Ha
Summary: The study developed a catalyst with N-selectivity for the nitroso aldol reaction, using a quantum calculation. The reaction mechanism was determined and optimized, resulting in a high yield of the product with high enantioselectivity. The catalyst provides a less expensive and more environmentally friendly alternative for the reaction.
Article
Chemistry, Organic
Daeil Bae, Jin Won Lee, Do Hyun Ryu
Summary: New bifunctional secondary amine organocatalysts derived from L-proline were synthesized and applied in enantioselective Michael reactions in water, yielding high product yields and stereoselectivity. Investigations on the effect of phenyl group at (R)-C6 in the catalyst were conducted, and the successful formal synthesis of a novel histamine H3 receptor agonist, Sch 50971, demonstrated the synthetic utility of this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hiroshi Ito, Yuya Yoshida, Tsuguya Masuda, Aiko Sasaki, Kyosuke Imoto, Kohei Sato, Tetsuo Narumi, Nobuyuki Mase
Summary: Fluorescent sensors were used to monitor chemical transformations with increased fluorescence intensity, enabling rapid identification of excellent organocatalytic systems. Through the analysis of data from over 4,000 screenings, a combination of pyrrolidine and isophthalic acid was found to be a catalyst template for the quaternary carbon-containing aldol reaction. After fine-tuning of the catalyst template, 5-hydroxy isophthalic acid was confirmed as a highly reactive additive.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sedigheh Sadat Naeimi, Peyman Salehi, Morteza Bararjanian
Summary: The synthesis of prolinamide derivatives of (R)-tetrahydropapaverine and their application as organocatalysts in asymmetric Aldol reaction were reported. Catalyst 2 showed the best catalytic activity in the reaction between cyclohexanone and 4-nitrobenzaldehyde, achieving up to 90% enantiomeric excess. Unlike the anti-stereoselectivity observed in the presence of L-proline alone, the hybridization with (R)-tetrahydropapaverine resulted in the formation of syn products as the major compounds.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yujiro Hayashi
Summary: The aldol reaction is a significant carbon-carbon bond-forming reaction in organic chemistry. The use of trifluoromethyl-substituted diarylprolinol as an organocatalyst has been found to be effective in promoting cross-aldol reactions with excellent selectivities.
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
Zubeda Begum, Haruka Sannabe, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano
Summary: Simple primary beta-amino alcohols act as efficient organocatalysts in the asymmetric Michael addition of beta-keto esters with nitroalkenes, producing highly pure chiral Michael adducts. The choice of catalyst and reaction temperature determines the enantiomeric outcome of the adducts.
Article
Biochemistry & Molecular Biology
Ciril Jimeno
Summary: The research was inspired by the binding and stabilizing effect of arginine residues in certain aldolases, leading to the development of a new family of amino acylguanidine organocatalysts. Screening and optimization identified the threonine derivative as the most suitable catalyst for asymmetric aldol addition, while the proline derivative yielded the anti diastereomer. MMFF models indicated the presence of an extensive hydrogen bonding network between the acylguanidinium group and the reaction intermediates.
Article
Chemistry, Multidisciplinary
Jason Fang, Laura E. Turner, Michelle C. Y. Chang
Summary: Fluorine is a critical element in designing bioactive compounds, but the synthesis of stereogenic tertiary fluorides is challenging and limited to a few approved drugs. In this study, the aldol reaction of fluorinated donors catalyzed by HpcH and engineered variants was found to generate enantiopure secondary and tertiary fluorides. This method not only represents the first synthesis of tertiary fluorides via biocatalysis but also increases the diversity of fluorinated building blocks and enables the synthesis of fluorinated drug analogs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Gen-Fa Wen, Rui Zhang, Chu-Yu Zhang, Chao-Shan Da
Summary: This study compares and explores the catalytic efficiencies of structurally similar alpha- and beta-amino acids in an asymmetric aldol transformation. The results show that both types of amino acids achieve high catalytic efficiencies under different optimal conditions, and in some cases, the beta-amino acid even exhibits higher enantioselectivity than the alpha-amino acid.
SYNTHESIS-STUTTGART
(2023)
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
Chemistry, Physical
Carlos Lizandara-Pueyo, Xinyuan Fan, Carles Ayats, Miquel A. Pericas
Summary: This study involved the controlled synthesis of calcium carbonate particles surface-functionalized with azido groups, followed by copper-catalyzed alkyne-azide cycloaddition reactions to prepare novel catalytic materials. The immobilized catalyst demonstrated high selectivity and efficiency in catalyzing Michael addition reactions of aldehydes, with the added advantage of being reusable and adaptable to continuous-flow operation for increased productivity.
JOURNAL OF CATALYSIS
(2021)
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, Organic
Shweta Bisht, Rashmi Rani, Rama Krishna Peddinti
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Arun Sharma, Rama Krishna Peddinti
Article
Chemistry, Organic
Balakrishna Aegurla, Rama Krishna Peddinti
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Jyoti Singh Tomar, Rama Krishna Peddinti, Ramakrishna V. Hosur
BIOCHEMICAL JOURNAL
(2019)
Article
Chemistry, Organic
Balakrishna Aegurla, Rama Krishna Peddinti
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Jyoti Agarwal, Rama Krishna Peddinti
Article
Chemistry, Organic
Neha Dua, Sonali Ghosh, Rama Krishna Peddinti
Summary: A novel method using zinc triflate-catalyzed regioselective 1,6-conjugate addition has been developed for synthesizing 3,3-diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic acid esters. The protocol yields hybrid compounds in good to excellent yields, with rapid reaction kinetics and broad substrate scope.
Article
Chemistry, Organic
Deepti Gairola, Rama Krishna Peddinti
Summary: The Friedel-Crafts reaction is commonly used for C-C bond formation, allowing the direct connection of electron-rich arenes to electron-deficient olefins with high regioselectivity. A metal-free and environmentally friendly strategy using methanesulfonic acid as a green reagent was developed for the synthesis of 3-arylsuccinimides from electron-rich arenes and N-arylmaleimides under mild conditions, showing high efficiency and compatibility with different substrates.
SYNTHESIS-STUTTGART
(2021)
Correction
Chemistry, Organic
Arun Sharma, Jyoti Agarwal, Rama Krishna Peddinti
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Pallavi Singh, Rama Krishna Peddinti
Summary: This paper presents a highly efficient and sustainable synthesis of triarylmethanes through the dehydrative coupling of p-quinols with diaryl carbinols. The catalyst used in this protocol is the in situ generated superacid BF3-H2O from BF3-OEt2. Moisture is used as an efficient initiator in this reaction system, and various diaryl carbinols and p-quinols have been found to be compatible, yielding triarylmethanes with up to 96% yield.
JOURNAL OF CHEMICAL SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Pallavi Singh, Rama Krishna Peddinti
Summary: This new method provides an efficient and atom-economic strategy for the synthesis of thioesters from readily available and inexpensive starting materials. It avoids the use of expensive and hazardous coupling reagents, bases, and generates water as the only by-product, making it more viable and environmentally friendly for sustainable chemistry.
JOURNAL OF CHEMICAL SCIENCES
(2021)
Article
Chemistry, Organic
Balakrishna Aegurla, Nisha Jarwal, Rama Krishna Peddinti
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Neha Dua, Rama Krishna Peddinti
JOURNAL OF CHEMICAL SCIENCES
(2020)
Article
Chemistry, Organic
Piyush Tehri, Rama Krishna Peddinti
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Nitika Sharma, Rama Krishna Peddinti
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)