An efficient direct aldol reaction between coumaran-3-ones and β, γ-unsaturated α-ketoesters by virtue of a chiral copper complex is developed. A series of coumaran-3-one derivatives containing chiral tertiary alcohol structures are obtained in excellent yields and stereoselectivities.
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http://dx.doi.org/10.1002/chem.202003510 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Changchun Institute of Applied Chemistry Chinese Academy of Sciences: Chang Chun Institute of Applied Chemistry Chinese Academy of Sciences, Jilin Province Key Lab of Green Chemistry and Process, CHINA.
A modular approach was developed for the first catalytic asymmetric total syntheses of naturally occurring C30 terpene quinone methides and their non-natural stereoisomers, which feature the presence of an unprecedented spiro[4.4]nonane-containing 6-6-6-5-5-3 hexacyclic skeleton. Resting on a chiral phosphinamide-catalyzed enantioselective reduction of 2,2-disubstituted cyclohexane-1,3-dione, a concise route for the synthesis of enantioenriched 6-6 bicyclic fragment was developed.
View Article and Find Full Text PDFMini Rev Med Chem
January 2025
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Johor, Malaysia.
Indole, a ubiquitous structural motif in bioactive compounds, has played a pivotal role in drug discovery. Among indole derivatives, indole-3-carboxaldehyde (I3A) has emerged as a particularly promising scaffold for the development of therapeutic agents. This review delves into the recent advancements in the chemical modification of I3A and its derivatives, highlighting their potential applications in various therapeutic areas.
View Article and Find Full Text PDFRSC Adv
November 2024
School of Biological and Environmental Engineering, Chaohu University, Chaohu Regional Collaborative Technology Service Center for Rural Revitalization Hefei Anhui 238000 China
Aldehydes have been proposed as important precursor species in new particle formation (NPF). Although formaldehyde (CHO) has minimal direct involvement in sulfuric acid (HSO) and water nucleation, it remains unclear whether its atmospheric aldol condensation product, hydroxyacetaldehyde (CHO), one of the simplest bifunctional oxygenated volatile organic compounds (OVOCs), plays a role in NPF. This study investigates both the aldol condensation of CHO and its role in NPF involving HSO and CHO through quantum chemical calculations and atmospheric cluster dynamics modeling.
View Article and Find Full Text PDFMacromol Rapid Commun
November 2024
PCFM, LIFM Lab and GD HPPC Lab, School of Chemistry, Sun Yat-sen University, Guangzhou, 510275, P. R. China.
Nanostructures with curved surfaces and chiral-directing residues are highly desirable in the synthesis of asymmetric chemicals, but they remain challenging to synthesize without using unique templates due to the disfavored torsion energy of twisted architectures toward chiral centers. Here, a strategy for the facile fabrication of highly cured capsule-shaped catalysts with chiral interiors by the amplification of molecular chirality via the irreversible cross-linking of 2D asymmetric laminates is presented. The key to the success of these irregular 2D layers is the use of hierarchical assembly of chiral macrocycles, which can exactly regulate the cured nanostructures as well as asymmetric catalysis.
View Article and Find Full Text PDFOrg Lett
November 2024
Department of Chemistry, Indian Institute of Science Education & Research Bhopal, Bhopal, Madhya Pradesh 462066, India.
A new synergistic Rh(II)/Zn(II)-catalyzed [3 + 3] annulation has been developed between diazoenals and α-hydroxy ketones enabling the direct synthesis of 4-formyl-2-pyrans. The reaction involves the formation of protic oxonium ylides from highly electrophilic Rh-enalcarbenoids followed by Zn-templated regioselective intramolecular aldol condensation. Subsequent investigations demonstrated that 4-formyl-2-pyrans are unique precursors of γ-pyrones.
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