Revolutionizing C –H Activation Reactions: Harnessing Green Solvents for Sustainable Catalysis
Conclusion [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - February 12, 2024 Category: Chemistry Authors: Deshmukh, Dewal Vagadiya, Nikunjkumar Jagtap, Samadhan Malasane, Pravin Tags: short review Source Type: research
Rapid Access to cis-1,3-Dialkylindanes: Asymmetric Formal Syntheses of epi-Mutisianthol and epi-Jungianol
Synthesis DOI: 10.1055/a-2249-2326 Concise and strategically unique asymmetric formal syntheses of epi-mutisianthol and epi-jungianol are presented. A novel disconnection approach is introduced to complement previous intramolecular cyclopentannulation strategies. Noteworthy features include: (a) control of the stereogenic benzylic carbon center through 1,3-chirality transfer from chiral indenols via the Johnson–Claisen rearrangement, which yields advanced indene-containing γ,δ-unsaturated esters, and (b) the diastereoselective construction of the cis-1,3-dialkylindane backbone via catalytic hydrogenation of the resulti...
Source: Synthesis - February 12, 2024 Category: Chemistry Authors: Tran, Cong So Yoon, Moonsang Le, Long Duc Kim, Seoyeong Kim, Huiae Kim, Jisu Nguyen, Long Huu Koh, Minseob Yun, Hwayoung Tags: paper Source Type: research
Solvent-Free Efficient Synthesis of New 4-Thiazolidinones with a Fructose Scaffold through a Microwave-Assisted Cascade Multicomponent Reaction
Synthesis DOI: 10.1055/a-2231-4922 Using a chemoselective, sustainable and highly efficient method, new 4-thiazolidinones and 1,4-thiazepan-3-ones substituted with a glycosidic residue derived from d-fructose were synthesized. Microwave-assisted cascade multicomponent reaction under solvent-free conditions gave very good yields in short reaction times, which was followed by a nontoxic purification method of one of the diastereomers by precipitation–centrifugation. The new purified compounds isolated as diastereomers were evaluated as factor Xa (FXa) inhibitors. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stutt...
Source: Synthesis - February 12, 2024 Category: Chemistry Authors: Lorenzo, Fernando Ocampo, Romina Rodr Ãguez, Diego F. Santana-Romo, Fabi án Galdamez, Antonio Zacconi, Flavia C. Burrow, Robert A. Mandolesi, Sandra D ’Accorso, Norma Tags: paper Source Type: research
Iodine-Promoted Disproportionate Coupling Reaction of Arylsulfonyl Hydrazides: A Simple and Green Access to Thiosulfonates
Synthesis DOI: 10.1055/a-2248-5438 An environmentally friendly iodine-promoted disproportionate coupling reaction of arylsulfonyl hydrazides is reported. This strategy can synthesize thiosulfonates with medium to excellent yields, and features a green system, wide applicability of substrates, and easy availability of raw materials. The preliminary mechanistic study reveals that iodine plays an important role in the radical reaction process. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - February 12, 2024 Category: Chemistry Authors: Chen, Qi Chen, Zhao-Hua Liang, Yong-Tong Zeng, Yong Yu, Shi-Wei Yang, Kai Wang, Zhao-Yang Tags: paper Source Type: research
Synthesis of Thiazole-fused Tricyclic Quinazolinone Alkaloids and Their Derivatives
Synthesis DOI: 10.1055/a-2243-4727 The synthesis of thiazole-fused derivatives of tricyclic quinazolinones hitherto undescribed was successfully achieved by replacing anthranilic acid or its derivatives by isomeric polyfunctionalized benzothiazole analogues of anthranilic methyl esters. Some of the new heterocyclic systems are inspired by natural alkaloids such as mackinazolinone, deoxyvasicinone, and isaindigotone, showing interesting biological properties. The microwave-assisted method developed is a variant of the Niementowski reaction and was also applied to the synthesis of ring-extended rutaecarpine derivatives. [......
Source: Synthesis - February 12, 2024 Category: Chemistry Authors: Broudic, Nathan Layec, Corentin Fruit, Corinne Besson, Thierry Tags: paper Source Type: research
Tertiary Amines as Temporary Masked Secondary Amines: A Direct Access to 5-Dialkylamino-1,2,4-oxadiazoles from 1,2,4-Oxadiazol-5(4H)-ones
Synthesis DOI: 10.1055/s-0042-1751555 A novel strategy utilizing tertiary amines as temporary masked secondary amines to synthesize 5-dialkylamino 1,2,4-oxadiazoles via Ph3P-I2 mediated amination of 1,2,4-oxadiazol-5(4H)-ones was developed. A one-step N-dealkylative functionalization of tertiary amines with the 1,2,4-oxadiazole ring enables a convenient access to diverse 5-amino-1,2,4-oxadiazoles. Additionally, orthogonally functionalized piperazine derivatives can be effectively constructed through site-selective reaction of 1,4-dialkylpiperazines or via a sequential N-functionalization of 1-methylpiperazine obviating lab...
Source: Synthesis - February 12, 2024 Category: Chemistry Authors: Alfliadhi, Muh Pattarawarapan, Mookda Hongsibsong, Surat Wiriya, Nittaya Phakhodee, Wong Tags: paper Source Type: research
Organocatalytic Atroposelective Reactions of Alkynes
Conclusion and Outlook [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - February 8, 2024 Category: Chemistry Authors: Zhang, Zhi-Xin Hu, Tian-Qi Ye, Long-Wu Zhou, Bo Tags: short review Source Type: research
Copper-Catalyzed Enantioselective Radical Esterification of Propargylic C –H Bonds
Synthesis DOI: 10.1055/a-2240-5349 The copper-catalyzed enantioselective radical esterification of propargylic C–H bonds with tert-butyl peroxybenzoate (TBPB) as an oxidizing agent and an oxygenated nucleophile is reported. This variant of the Kharasch–Sosnovsky oxidation allows for the asymmetric esterification of open-chain carbon radicals without excessive amounts of alkyne substrates under mild reaction conditions, achieving a one-step conversion of simple alkynes into chiral propargylic esters. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents ...
Source: Synthesis - February 8, 2024 Category: Chemistry Authors: Xi, Jiajia Zhu, Xiaotao Bao, Hongli Tags: paper Source Type: research
Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent
Synthesis DOI: 10.1055/s-0043-1763675 A new synthetic approach for the preparation of amides and peptides containing amino acids as well as aryl acids and amines by employing [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF) as a carboxylic acid activator under mild conditions is delineated. The use of AISF as an acid activator allows the reaction to be performed efficiently. This operationally simple amidation is amenable to a wide variety of carboxylic acids and Nα-protected amino acids. Further, racemization did not occur during the coupling. In addition, a gram-scale reaction is demonstrated. [...] Georg Thieme...
Source: Synthesis - February 8, 2024 Category: Chemistry Authors: Bharamawadeyar, Swetha Chetankumar, Eti Srinivasulu, Chinthaginjala Sureshbabu, Vommina V. Tags: paper Source Type: research
An Improved and Scalable Synthesis of the Potent SREBP Inhibitor KK-052 via [3+2] Cycloaddition
Synthesis DOI: 10.1055/a-2236-0413 KK-052 is a novel vitamin-D-based selective sterol regulatory element-binding protein (SREBP) suppressor that lacks vitamin D genomic activity mediated through the vitamin D receptor in both in vitro and in vivo settings. In our initial synthetic effort, KK-052 was produced as one of the structural isomers obtained via the Mitsunobu reaction involving a CD-ring allyl alcohol and 5-phenyl-1H-tetrazole. In this work, we present a refined methodology for enhancing the selective synthesis of KK-052 through a [3+2] cycloaddition between a CD-ring benzimidoyl chloride and sodium azide, a techni...
Source: Synthesis - February 7, 2024 Category: Chemistry Authors: Kawagoe, Fumihiro Mototani, Sayuri Takemoto, Yasushi Uesugi, Motonari Kittaka, Atsushi Tags: paper Source Type: research
Metal-Free N-Formylation of Amines Using Carbohydrates as C1 Synthon via C –C Bond Cleavage
Synthesis DOI: 10.1055/a-2241-6697 Formamide group is an important part of many drug molecules, and herein a process for N-formylation of amines using carbohydrates as the C1 synthon under oxidative metal-free reaction conditions has been reported for the first time. Literature syntheses of formamides uses toxic, moisture sensitive and costly reagents under harsh reaction conditions. Our metal-free formylation is a facile, economical, and an efficient process of broad substrate scope that has led to the synthesis of thirty-three N-formylated compounds in excellent isolated yields. [...] Georg Thieme Verlag KG RüdigerstraÃ...
Source: Synthesis - February 7, 2024 Category: Chemistry Authors: Atpadkar, Shital Gill, Manjinder Singh Tags: paper Source Type: research
LiO-t-Bu/CsF-Mediated Formal Hydrolysis of Trifluoromethyl Arenes
This study investigates the formal hydrolysis of trifluoromethyl arenes without deprotonation functionality utilizing a combined Brønsted base system comprising LiO-t-Bu and CsF. The reaction conditions were optimized using 4-(trifluoromethyl)biphenyl as the model substrate, achieving a 94% yield with LiO-t-Bu/CsF. The scope of the substrate was explored, demonstrating the applicability of the system to various functionalities, such as (hetero)aryl, tert-butyl, methyl, amide, and alkenyl moieties. Mechanistic insights suggest a single electron transfer process. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttg...
Source: Synthesis - February 1, 2024 Category: Chemistry Authors: Shigeno, Masanori Kiriyama, Moe Izumi, Koki Sasaki, Keita Sasamoto, Ozora Nozawa-Kumada, Kanako Kondo, Yoshinori Tags: paper Source Type: research
Organocatalytic Approach to the Enantioselective Total Synthesis of (+)-Serinolamides A and B and (+)-Lacosamide
Synthesis DOI: 10.1055/a-2222-3822 A short and highly efficient enantioselective synthesis of (+)-serinolamide A, B and (+)-lacosamide from 3-methoxypropanal using l-proline-catalyzed α-amination, Grubbs metathesis, and acid-amine coupling as key steps is reported. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - January 31, 2024 Category: Chemistry Authors: Jadhao, Amardeep R. Waghmode, Suresh B. Tags: paper Source Type: research
Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes
Synthesis DOI: 10.1055/a-2236-8874 Alumina was found to activate Cu(I) catalysts in hydroboration of alkynes. This allowed to develop a simple and efficient protocol for hydroboration of alkynes with B2Pin2 using inexpensive CuCl/PPh3 catalytic system. The approach does not require moisture-sensitive activators and stepwise preparation of ‘activated’ Cu complex. The developed conditions were applied to the preparation of β-styrylboronates from terminal and internal alkynes with excellent regio- and stereoselectivity. The procedure can also be extended to other terminal alkynes by the appropriate choice of ligand. [......
Source: Synthesis - January 31, 2024 Category: Chemistry Authors: Barashkova, Xenia A. Parulava, Mikhail J. Kotovshchikov, Yury N. Latyshev, Gennadij V. Lukashev, Nikolay V. Beletskaya, Irina P. Tags: paper Source Type: research
Stereodivergent Carbon –Carbon Bond-Forming Reactions
Conclusions and Outlook [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - January 29, 2024 Category: Chemistry Authors: Healy, Alan R. Tags: short review Source Type: research
