Aliphatic and aromatic sulfonamides were alkynylated with 1-bromo-1-alkynes in the catalytic presence of CuI to give N-(1-alkynyl)sulfonamides in good to excellent yields. The acetylene-titanium complexes generated from N-(1-alkynyl)benzosultams underwent diastereoselective addition to aldehydes. [reaction: see text]
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol036396b | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp)-H Phosphorylation of Bicyclo[1.1.0]butanes.
Org Lett
January 2025
Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing, 210095, P. R. China.
Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives.
View Article and Find Full Text PDFCatalytic Enantioselective Synthesis of 1,4-(Hetero) Dicarbonyl Compounds through α-Carbonyl Umpolung.
J Am Chem Soc
January 2025
Institute of Organic Chemistry, University of Leipzig, 04103 Leipzig, Germany.
The enantioselective synthesis of 1,4-dicarbonyl compounds continues to pose a significant challenge in organic synthesis, and a catalytic process which generates two adjacent stereogenic centers with full stereochemical control is lacking until now. The 1,4-relationship of the functional groups requires an Umpolung strategy as one of the α-carbonyl positions has to be inverted into an electrophilic center to react with a normal enolate. We report herein the highly enantio- and diastereoselective addition of silyl ketene acetals toward electrophilic 1-azaallyl cations to furnish chiral 4-hydrazonoesters, which are masked 1,4-dicarbonyl compounds.
View Article and Find Full Text PDFConcise Synthesis of (-)-Veratramine and (-)-20--Veratramine via Aromative Diels-Alder Reaction.
J Am Chem Soc
January 2025
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
A concise and convergent synthesis of the isosteroidal alkaloids veratramine and 20--veratramine has been accomplished. A Horner-Wadsworth-Emmons olefination joins two chiral building blocks of approximately equal complexity and a transition-metal catalyzed intramolecular Diels-Alder cycloaddition-aromatization cascade constructs the tetrasubstituted arene. Other key steps include a highly diastereoselective crotylation of an -sulfonyl iminium ion and an Eschenmoser fragmentation.
View Article and Find Full Text PDFEnantioselective Synthesis of Nonfused Eight-Membered O-Heterocycles by Sequential Catalysis.
Org Lett
January 2025
Catalytic Hydrogenation Research Center, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
This work describes a chiral bifunctional squaramide/DBU sequential catalytic strategy for the enantioselective synthesis of nonfused chiral eight-membered O-heterocycles through the asymmetric addition of ynones to β,γ-unsaturated α-ketoesters followed by the regio- and diastereoselective cyclization of the adduct intermediates. Mechanistic experiments revealed that an isomerization process should be involved in the ring formation step, and the origin of the high regioselectivity and diastereoselectivity has also been elucidated by the DFT calculations.
View Article and Find Full Text PDFDiastereoselective Construction of Bridged Azabicyclo[3.2.1]octane via Copper-Catalyzed Formal [4 + 3] Cycloaddition.
J Org Chem
January 2025
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, People's Republic of China.
A novel copper-catalyzed formal diastereoselective [4 + 3] cycloaddition of 2-arylaziridines and 2-substituted cyclopentadiene was developed. This transformation provided an efficient protocol for the assembly of a highly strained bridged azabicyclo[3.2.
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!