Article
Chemistry, Applied
Fabian Scharinger, Matthias Weil, Michael Schnuerch, Katharina Bica-Schroeder
Summary: We introduce a simple method for the synthesis of chiral diazabicycloalkanes in a single reaction step. This method is applicable to a wide range of enals and has high functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Qijian Ni, Xuyang Wang, Da Zeng, Qianling Wu, Xiaoxiao Song
Summary: By using a chiral bifunctional squaramide catalyst, an asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been achieved, providing an efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.
Article
Chemistry, Organic
Chandrakanta Parida, Buddhadeb Mondal, Animesh Ghosh, Subhas Chandra Pan
Summary: A novel organocatalytic asymmetric synthesis method for spirooxindole embedded oxazolidines has been developed using a specific catalyst, resulting in good diastereoselectivity and high enantioselectivity of the products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Fushuai Li, Zhihong Yang, Yanyan Yang, Qiuhong Huang, Xuling Chen, Pengfei Li, Mingxin Dong, Wenjun Li
Summary: A chiral phosphorus acid catalyzed enantioselective 1,4-conjugate addition of arylamines to in situ formed 7-methylene-7H-indoles from 7-indolylmethanols has been successfully developed for the first time without the use of additives. The catalytic protocol enables the formation of 1,4-adducts with a nitrogen-containing tertiary carbon stereocenter in moderate to high yields and good enantioselectivity under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Nengzhong Wang, Zugen Wu, Junjie Wang, Nisar Ullah, Yixin Lu
Summary: The past two decades have seen remarkable growth of asymmetric organocatalysis, serving as a powerful platform for producing chiral molecules. Ring structures are widely present in organic compounds, and strategic construction of ring motifs is crucial in natural product synthesis.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Michael J. Tilby, Damien F. Dewez, Adrian Hall, Carolina Martinez Lamenca, Michael C. Willis
Summary: In this study, the absolute configuration of sulfur-stereogenic aza-sulfur derivatives was determined using a unique feature of sulfonimidamides. Enantioselective alkylation was achieved by generating prochiral ions from sulfonimidamides with the help of a bis-quaternized phase-transfer catalyst. This demonstrates the potential of using configurationally labile aza-sulfur species in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Laura A. Bryant, Kenneth Shankland, Hannah E. Straker, Callum D. Johnston, Nicholas R. Lees, Alexander J. A. Cobb
Summary: The article describes a rare organocatalytic intramolecular cyclization of resorcinols with a high enantioselectivity using a specific organocatalyst. The obtained bicyclic resorcinols show excellent utility in the synthesis of cannabinoid-like compounds, and exhibit anticonvulsant activity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Pengyan Wang, Junhan Chen, Weigang He, Jiacheng Song, Hengqian Song, Hongbo Wei, Weiqing Xie
Summary: A concise asymmetric synthesis of (divided by)-isostrychnine is achieved through nine longest-linear steps with a 16% overall yield. Key features include catalytic asymmetric tandem double Michael addition, intramolecular dehydrative condensation/lactamization reaction, and allylic diazene rearrangement.
Article
Chemistry, Applied
Andrea Guerrero-Corella, Miguel A. Valle-Amores, Alberto Fraile, Jose Aleman
Summary: An asymmetric organocatalytic aza-Michael addition reaction of ketimines to nitroolefins is described, utilizing 2-hydroxybenzophenone imine to improve the enantioselective addition of N-centered nucleophiles to nitroalkenes. The versatility of the process is demonstrated under both batch and flow conditions, resulting in the synthesis of a wide variety of nitroamine derivatives with excellent yields and enantioselectivities. Additionally, this methodology was successfully applied to the formal synthesis of VNI, a drug-like scaffold for the treatment of Chagas disease.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Ruiying Ma, Hongzhou Yang, Ling Ye, Qiang Yang, Zhichuan Shi, Zhigang Zhao, Xuefeng Li
Summary: A one-pot, two-step aza-Michael/Michael/Michael process has been developed for the diastereospecific construction of C6a,C10acis-hydrophenanthridines in a highly enantioselective manner (83-99% ee). The tricyclic products were obtained in 50-99% isolated yields, sequentially promoted by bifunctional squaramide and diamine in a one-pot operation. This doubly annulative protocol demonstrates the facile construction of complex polycyclic structures through the full utilization of available reaction sites in readily prepared precursors.
Article
Chemistry, Organic
Zhi-Hao You, Sheng Zou, Ya-Li Song, Xue-Qing Song
Summary: An organocatalyzed asymmetric synthesis of fused butyrolactones has been established via a one-pot process. The reaction involves the formal [2 + 2 + 2] annulation between gamma-butenolides, methylene indolinones, and nitroolefins. The L tertleucine-derived bifunctional thiourea catalyst provides good yields (up to 95%) and excellent enantioselectivities (up to >99% ee).
Article
Chemistry, Organic
Chandan Gharui, Chandrakanta Parida, Subhas Chandra Pan
Summary: An organocatalytic asymmetric addition reaction of aromatic alpha-cyanoketones to in situ-generated o-quinone methides was successfully developed, leading to the synthesis of 3,4-dihydrocoumarin and tetrasubstituted chroman products. The desired products were obtained with high enantio- and diastereoselectivities under 10 mol % catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dmitri Trubitson, Jevgenija Martonova, Marina Kudrjasova, Kristin Erkman, Ivar Jarving, Tonis Kanger
Summary: An efficient enantioselective organocatalytic method has been developed for the synthesis of N-alkylated indoles with alpha-branched alkyl substituents from unsaturated indolyl ketones via a Michael addition. The resulting products exhibit high enantioselectivities and good yields, with tolerance towards various nucleophiles and substitution patterns of the indole ring. Both electron-withdrawing and electron-donating substituents can be accommodated at any position of the heteroaromatic ring.
Article
Chemistry, Organic
Ahreum Kim, Junsoo Moon, Chanhee Lee, Jayoung Song, Jongchan Kim, Yongseok Kwon
Summary: In this study, a highly enantioselective Pictet-Spengler reaction for the synthesis of axially chiral tetrahydroisoquinolines via dynamic kinetic resolution is reported. The cyclization catalyzed by chiral phosphoric acids leads to the formation of single regioisomeric isoquinolines with excellent enantioselectivities up to 99% ee around the C-C bond. The effectiveness of this protocol is demonstrated for a wide range of substrates, with enantiodivergence observed depending on the substituents on the catalysts.
Article
Chemistry, Multidisciplinary
Xiu-Ning Hu, Dong-Ping Wu, Ye-Peng Xu, Pei-Qiang Huang
Summary: The first organocatalytic asymmetric synthesis of an advanced intermediate of (+)-sarain A was achieved by combining organocatalytic asymmetric Michael addition reaction and a nitrogen-to-carbon chirality transfer. This method allows for the construction of three chiral centers and chemoselective reduction of a key lactam intermediate, providing a tricyclic intermediate with all necessary functionalities for further elaboration into (+)-sarain A.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
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)
