Article
Chemistry, Physical
Shiyu Sun, Changgong Xu, Jamielyn Jarvis, Phillip Nader, Brandon Naumann, Abigail Soliven, Roberto Peverati, Norito Takenaka
Summary: A new class of axial-chiral biisoquinoline N,N'-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. Although these catalysts showed poor to moderate reactivity and enantioselectivity, this study represents the first example of organocatalytic asymmetric reduction of acyl hydrazones. Additionally, the structures and energies of two possible diastereomeric catalyst-trichlorosilane complexes were analyzed using density functional theory calculations.
Article
Chemistry, Organic
Kirill K. Popov, Joanna L. P. Campbell, Ondrej Kysilka, Jan Hosek, Christopher D. Davies, Milan Pour, Pavel Kocovsky
Summary: In this study, Aldimines generated from various aldehydes and amines can be reduced using trichlorosilane in the presence of dimethylformamide as an organocatalyst. The reaction tolerates a wide range of functional groups and offers advantages over traditional methods in terms of efficiency and chemoselectivity. The use of DMA as a greener alternative to DMF is also explored.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qiang Wang, Tomas Nilsson, Lars Eriksson, Kalman J. Szabo
Summary: The reported method allows for the synthesis of densely functionalized chiral allyl compounds with high stereo-, diastereo- and site-selectivity based on selenium-catalyzed sulfenofunctionalization of chiral alpha-CF3 allylboronic acids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Izabela Weglarz, Karol Michalak, Jacek Mlynarski
Summary: The study reported the first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex, achieving pharmaceutically relevant enantioenriched 2-aryl-substituted pyrrolidines with excellent enantioselectivities. The synthetic utility of the presented methodology was demonstrated in an efficient synthesis of pharmaceutical drug precursors to Aticaprant and Larotrectinib.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Aliyaah J. M. Rahman, Lucie Finck, Wolfgang Obermayer, Martin Oestreich
Summary: The transition-metal-free protocol allows for the arylation of N-phenyl and N-benzoyl-substituted, benzaldehyde-derived imine derivatives with functionalized aryl pronucleophiles. Aryl nucleophiles are released from silicon protected aryl-substituted diazenes through desilylation with potassium trimethylsilanolate, simultaneously losing dinitrogen.
Article
Chemistry, Multidisciplinary
Ben-Xian Xiao, Bo Jiang, Ru-Jie Yan, Jian-Xiang Zhu, Ke Xie, Xin-Yue Gao, Qin Ouyang, Wei Du, Ying-Chun Chen
Summary: Palladium(0) complexes can coordinate with 1,3-dienes in an eta(2) fashion, raising the energy of their HOMO to enable a hydrodienylation reaction. Additionally, a vinylogous addition/allylic alkylation difunctionalization process can also take place.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Qingqing Luo, Zhou Tian, Jie Tang, Jie Wang, Yin Tian, Cheng Peng, Gu Zhan, Bo Han
Summary: The study focuses on the design of bifunctional 4-pyrrolidinopyridines as Lewis base catalysts, which exhibited excellent efficiency and stereoselectivity in asymmetric cycloaddition reactions. The research provides strong support for the construction of chiral spiropyrazolone derivatives.
Article
Chemistry, Organic
Hyoung Min Yeo, Sungmin Kang, Taek Hyeon Kim
Summary: The first chiral proline amide-isothiouronium based bifunctional organocatalyst was developed, showing high to quantitative yields in aldol products with excellent control performance of diastereoselectivities and enantioselectivity.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Julien Braire, Aurelie Mace, Rania Zaier, Marie Cordier, Joelle Vidal, Claudia Lalli, Arnaud Martel, Francois Carreaux
Summary: An improvement in the catalytic enantioselective allylboration of isatins with 2-allyl-1,3,2-dioxaborolane in the presence of chiral BINOL derivatives is reported. The high enantioselectivity of this reaction is due to the internal hydrogen bonding and the addition of alcohol additive, as shown by DFT calculations and kinetics study.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Julien Braire, Aurelie Mace, Rania Zaier, Marie Cordier, Joelle Vidal, Claudia Lalli, Arnaud Martel, Francois Carreaux
Summary: An improvement in the catalytic enantioselective allylboration of isatins with 2-allyl-1,3,2-dioxaborolane in the presence of chiral BINOL derivatives is reported, offering an efficient one-step access to enantioenriched N-unprotected 3-allyl-3-hydroxy-2-oxindoles. The origins of the high enantioselectivity and the key role of the alcohol additive have been investigated.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yuanyun Gu, Yan-En Wang, Yaqi Yuan, Haodong Xu, Yizhou Lu, Yufei Zhang, Fei Xue, Dan Xiong, Jianyou Mao
Summary: The deprotonation of allylbenzene was achieved using a catalytic alkali amide base, and the resulting allyl anion was trapped by N-(trimethylsilyl) aldimines to synthesize homoallylic amines. This one-pot method provided value-added products with excellent selectivity without the need for protection groups on the imines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hyoung Min Yeo, Take Hyeon Kim
Summary: The chiral proline amide-isothiouronium salt-based bifunctional organocatalyst, which has more acidic and active N-H bonds compared to thiourea, was prepared by methylating the corresponding chiral thiourea. This catalyst was used for the alpha-hydrazination of aldehydes using azodicarboxylates to produce beta-hydrazino alcohols, beta-amino alcohols, and alpha-amino acid derivatives. Enantioselective alpha-hydrazination of aldehydes was successfully carried out with the amide-isothiouronium salt as a chiral catalyst, resulting in high to quantitative yields and excellent enantioselectivities (up to 99% ee) of various hydrazino aldehydes in the presence of a benzoic acid additive.
Article
Chemistry, Organic
Congzheng Gu, Guangzheng Tian, Qingyu Yin, Fan Wu, Zhiming Li, Xiaoyu Wu
Summary: An enantioselective Mannich addition reaction of 3,5-disubstituted 4-nitroisoxazoles to beta,gamma-alkynyl-alpha-ketimino esters has been developed using an amide phosphonium salt-based catalyst. Chiral tertiary propargylic amine products were obtained with moderate to good yields and enantioselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Ryosuke Shimamoto, Akihiro Tsurusaki, Ken Kamikawa
Summary: Catalytic enantioselective 1,2-addition reactions of arylboronic acids with 1,2,5-thiadiazoline 1,1-dioxide derivatives were achieved using a planar-chiral phosphine-olefin ligand L5 with a bis[(2,3,4,5,6-pentafluoro)phenyl]phosphino group, resulting in <=98% ee. The addition product enantioselectivities were enhanced by introducing more fluoro substituents on the aromatic ring of the ligand. X-ray crystallographic studies of 3aa and [RhCl/L5]2 determined the absolute configuration of the enantioenriched addition product 3 and the bidentate coordination mode of L5 to a rhodium(I) cation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shutao Wang, Yongliang Gao, Shaoli Song, Xinze Li, Zhuoqi Zhang, Jinbao Xiang, Lianyou Zheng
Summary: This article describes a Lewis base catalyzed allylation reaction between N-aryl amides and various Morita-Baylis-Hillman (MBH) carbonates. The substrate scope of MBH carbonates and amides is comprehensively explored, making this approach useful for the synthesis of diversified branched tertiary N-allylic amides, with broad substrate scope, mild reaction conditions, and scalability.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
