A novel copper-catalyzed complete diastereoselective 1,2-difunctionalization of oxabicyclic alkenes has been developed. Two C-S bonds were constructed simultaneously on the oxabenzonorbornadienes leading to β-thiocyanato thioethers through the three-component (oxabicyclic alkenes, aryl iodides, and potassium thiocyanate), one-pot reaction. Various functional groups attached to the substrates were tolerated in this protocol to afford the corresponding β-thiocyanato thioether products in moderate yields.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.9b02452 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enantioselective Decarboxylative Mannich Reactions of α,β-Unsaturated β'-Ketoacids and Isatin Imines: Application in the Synthesis of Spiro[indoline-3,2'-piperidine]-2,4'-diones.
Org Lett
January 2025
Department of Chemistry, Memorial University, St. John's, Newfoundland and Labrador A1B 3X7, Canada.
Organocatalytic, enantioselective decarboxylative Mannich reactions of α,β-unsaturated β'-ketoacids and isatin -Boc imines, to give the corresponding 3-carbamoyl-2-oxindole derivatives, were developed. Subsequent N-deprotection and diastereoselective, intramolecular, aza-Michael reaction of the free amine provides previously unreported spiro[indoline-3,2'-piperidine]-2,4'-diones.
View Article and Find Full Text PDFSynthesis of Benzazepines Bearing Three Contiguous Carbon Stereocenters through Pd(II)-Catalyzed [3 + 2] Cycloaddition of -Aryl Nitrones with Allenoates.
J Org Chem
January 2025
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
A cascade reaction of Pd(II)/dppben-catalyzed [3 + 2] cycloaddition of -aryl nitrones with allenoates and sequential reduction has been developed for the synthesis of functionalized benzazepines bearing three contiguous carbon stereocenters in moderate to good yields ranging from 15 to 82% and high diastereoselectivity. The obtained benzazepines could be converted into various benzazepine scaffolds, and an estrone-derived benzazepine scaffold was prepared over four steps from estrone. More importantly, chiral benzazepine bearing three contiguous carbon stereocenters could be obtained in 88% ee value with chiral auxiliary.
View Article and Find Full Text PDFReactions of Tertiary Aliphatic Cations with Silylated Alkynes: Substitution, Cyclization and Unexpected C-H Activation Products.
Chemistry
January 2025
Université de Rennes 1, Chemistry, Equipe CORINT, Institut des Sciences Chimiques de Rennes, Université de Rennes 1 - UMR 6226 CNRS, Bâtiment 10A, Bureau 158, Avenue du Général Leclerc, 35042, Rennes, FRANCE.
Capozzi's groundbreaking work in 1982 introduced a fascinating reaction involving highly reactive tertiary aliphatic cations and silylated alkynes. This reaction provided an innovative solution to the challenge of coupling a fully substituted tertiary aliphatic fragment with an alkyne moiety. Building upon Capozzi's pioneering efforts, we started an extensive exploration of reaction conditions to expand the initial scope of this reaction.
View Article and Find Full Text PDFDiastereoselective Synthesis of Cyclobutanes via Rh-Catalyzed Unprecedented C-C Bond Cleavage of Alkylidenecyclopropanes.
Org Lett
January 2025
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
The stereoselective synthesis of highly substituted cyclobutanes is essential for the development of lead candidates in drug discovery. Herein, we present a novel Rh(III)-catalyzed reaction pathway for synthesizing substituted cyclobutanes, which involves a concerted N-C bond formation and C-C bond cleavage between 2-aryl quinazolinones and alkylidenecyclopropanes. Notably, the combination of Rh(III) catalyst and HFIP solvent plays a critical role in facilitating the formation of cyclobutane rings.
View Article and Find Full Text PDFA Stereoselective Oxidative Dimerization En Route to (-)-Lomaiviticin A.
Org Lett
January 2025
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
We describe a stereoselective synthesis of the dimeric diazofluorene , a potential precursor to the cytotoxic -symmetric bacterial metabolite (-)-lomaiviticin A (). An efficient route was developed to convert the tetracyclic diol to the diketone (five steps, 30% overall). Oxidative dimerization of the enoxysilane provided the -symmetric dimeric diazofluorene in 56% yield and with 15:1:0 diastereoselectivity.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!