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)
Article
Biochemistry & Molecular Biology
Victor V. Dotsenko, Alexander V. Aksenov, Anna E. Sinotsko, Ekaterina A. Varzieva, Alena A. Russkikh, Arina G. Levchenko, Nicolai A. Aksenov, Inna V. Aksenova
Summary: The Michael addition reaction between dithiomalondianilide and arylmethylidene Meldrum's acids, along with subsequent heterocyclization, was investigated. The study also looked into the factors affecting the composition of the obtained products. The structure of one of the products was confirmed through X-ray crystallography.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Review
Chemistry, Organic
Rekala Shalini Mamatha Jyothi, Mydhili P. P. Sripathi, Ponnaboina Thirupathi
Summary: The Michael addition is an important and efficient method for C-C bond formation, which has been widely used in the synthesis of natural products and drugs. This review provides comprehensive information on recent advancements in base-assisted Michael addition reactions.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Eugenia Marques-Lopez, Isaac G. Sonsona, Miryam Garces-Marin, M. Concepcion Gimeno, Raquel P. Herrera
Summary: In this study, the potential of phosphites as nucleophiles for the asymmetric synthesis of chiral chromene derivatives was explored. By employing asymmetric organocatalyzed phospha-Michael addition, chiral chromenylphosphonates were synthesized using a bifunctional squaramide. The optimized protocol provided good reactivity with yields of up to 95% and chiral products with an enantiomeric excess of up to 98%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Medicinal
Vitor Augusto dos Santos Garcia, Denise Osiro, Fernanda Maria Vanin, Cristiana Maria Pedroso Yoshida, Rosemary Aparecida de Carvalho
Summary: The purpose of this study was to develop oral films based on agar-agar incorporated with mushroom powder as a source of phenolic compounds. The oral films showed film-forming capacity and exhibited antioxidant properties. Furthermore, the oral films were found to be non-irritating to oral mucosa.
JOURNAL OF PHARMACEUTICAL SCIENCES
(2022)
Article
Chemistry, Organic
Cornelius Gaertner, Christoph Schneider
Summary: In this study, an asymmetric cooperative process is reported for the enantioselective 1,6-addition of fi-ketoesters to in situ generated para-quinone methides using chiral Pd-aqua complexes as mixed Bronsted acid-base catalysts. The reaction exhibits excellent yields, outstanding enantiocontrol, and good diastereoselectivity across a wide range of substrates. The utility of this reaction is demonstrated through facile scale up and subsequent complexity-increasing modifications.
Article
Chemistry, Organic
Ilya Nechaev, Georgij Cherkaev
Summary: An aerobic multicomponent reaction has been discovered to synthesize 3-arylsulfanyl-1-hydroxyindolizines, which can undergo different transformations under varied conditions. The presence of an O-uncapped indolizin-1-ol moiety modulates the redox properties, facilitating further chemical conversions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this study, a gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones was developed using an Al-Li-BINOL (ALB) complex catalyst. The reaction showed high diastereoselectivity with ratios up to 20:1 and enantioselectivity of 84-98% for various substrate combinations. This method is complementary to previous reports and improves selectivity for several chromones. Computational studies support the role of ALB as a bifunctional catalyst in this reaction and provide insights into the origin of the observed stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: A gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones, catalyzed by an Al-Li-BINOL (ALB) complex, was developed in this study. The diastereoselectivity reached 20:1 with 84-98% ee for various combinations of substrates. This protocol complements previous methods and improves selectivity for multiple chromones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Witsanu Sombat, Panassilp Authai, Panuwat Padungros, Voravee P. Hoven
Summary: Micellar systems have been recognized as effective nanoreactors for performing chemical reactions in aqueous solutions. This research developed nanoreactors from polymeric micelles, in which organic substrates were encapsulated and stabilized. The micellar nanoparticles assembled from PBAM-ran-PHPAM were spherical and well-dispersed in water, with a diameter of less than 170 nm. Thia-Michael addition reactions in the presence of the PBAM26-ran-PHPAM copolymer resulted in high conversions and isolated yields of the Michael adducts. The micellar nanoreactors were also reusable up to 10 times with a high reaction conversion of 75%.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Yuhao Yang, Gerald B. Hammond, Teruo Umemoto
Summary: A novel N-fluorosulfonamide reagent NFBB was developed for the high-yielding fluorination of active methylene compounds and the synthesis of highly basic (hetero)aryl and alkenyl compounds with unprecedented high or quantitative yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Misael Ferreira, Laieli S. Munaretto, Daniela P. Gouvea, Adailton J. Bortoluzzi, Marcus M. Sa
Summary: A method for the synthesis of a variety of functionalized 2-iminothiazolidines and related heterocycles through a base-mediated domino nucleophilic displacement/intramolecular anti-Michael addition process has been developed, showing good tolerance to different functional groups. The synthetic versatility of 2-iminothiazolidines was further demonstrated through a series of chemoselective modifications, leading to a wide range of thiazolidine frameworks of structural complexity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Alexandr O. Kokuev, Alexey Yu. Sukhorukov
Summary: A general transition metal-free synthesis of beta-hydrazonophosphine oxides was developed using the Michael addition of phosphine oxides R2P(O)H to reactive azoalkenes. The Z-isomers of beta-hydrazonophosphine oxides formed through this reaction are stabilized by intramolecular hydrogen bonding. The conversion of the products into potential chelating ligands was demonstrated.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Organic
Sanjay Singh, Ravi Saini, Ravi P. Singh
Summary: An unprecedented organocatalyzed asymmetric vinylogous Michael reaction with excellent enantiomeric ratio and yield has been reported. The remarkable selectivity is attributed to the hydrogen bonding ability of the catalyst. The reaction is versatile and practical for the synthesis of various gamma-functionalized coumarin derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Ralfs Pomilovskis, Inese Mierina, Anda Fridrihsone, Mikelis Kirpluks
Summary: In this study, new polymer materials were obtained by using previously developed acetoacetates and different bio-based monomers. These polymers have comparable qualities to polyurethanes without the need for hazardous materials or reactions under harsh conditions.
