Several additional examples of cascade cyclizations of α,β-unsaturated thioesters proceeding are reported, which proceed via two distinct mechanistic pathways: enantioselective acyl transfer promoted by amidine-based catalysts (ABCs) and a racemic chain mechanism mediated by a thiolate nucleophile.
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http://dx.doi.org/10.1021/acs.joc.0c02091 | 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 PDFOrg Biomol Chem
January 2025
School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China.
A visible-light-induced deoxygenative alkylation/cyclization of acrylamides with alcohols activated by CS has been developed by using xanthate salts as alkyl radical precursors in the presence of tricyclohexylphosphine. It proceeds through a tandem radical addition/cyclization process, and this protocol provides a reliable and practical approach to building the skeleton of 3,3-disubstituted oxindoles in moderate to good yields. Notable features of this reaction include readily available starting reagents, broad substrate scope and mild reaction conditions.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India.
The successful implementation of a cascade reaction involving a cyclobutyl unit has posed a significant challenge in achieving ring-retentive functionalization because of the ring's sacrificial tendency. Herein, we have accomplished a cinchona-derived squaramide-catalyzed cascade reaction sequence, encompassing the desymmetrization of cyclobutanone, followed by an aldol reaction and, subsequently, a 1,4-addition step. This overall process offers a viable strategy to access architecturally fascinating oxa-spirocycles fused with cyclobutanone motifs in good yields with high optical purity.
View Article and Find Full Text PDFChem Asian J
January 2025
IICT CSIR: Indian Institute of Chemical Technology, Organic Synthesis & Process Chemistry, Tarnaka, 500007, Hyderabad, INDIA.
A ferrocene-catalyzed cyanoalkylsulfonylative radical cascade cyclization of aryl 1,6-diynes using cycloketone oxime esters and DABCO.(SO₂)₂ (DABSO) is reported. The reaction proceeds with notable chemo- and regioselectivity, without requiring additional oxidants or reductants.
View Article and Find Full Text PDFRSC Adv
January 2025
College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Engineering Technology Research Center of Key Preparation Technology of Biomedical Polymer Materials Changde 415000 China.
Indole-fused pyridines are an important motif in pharmaceuticals and functional molecules. A visible-light induced Ru(bpy)Cl·6HO catalyzed radical cascade sulfonylation/cyclization strategy for the synthesis of indole-fused pyridine derivatives was developed. Diverse indole-fused pyridines bearing different functional groups were obtained in moderate to good yields.
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