Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo202199g | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Regioselective [3 + 2] Annulation of β,γ-Alkynyl-α-ketimino Esters with 1,3-Dicarbonyls: The Synthesis of Highly Functionalized Dihydrofurans.
J Org Chem
January 2025
Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, Laboratory of Optic-electric Chemo/Biosensing and Molecular Recognition, Education Department of Guangxi Zhuang Autonomous Region, Guangxi Minzu University, Nanning 530006, China.
A regioselective [3 + 2] annulation of β,γ-alkynyl-α-ketimino esters with 1,3-dicarbonyls is disclosed. A series of -selective dihydrofurans bearing an exocyclic double bond and a quaternary carbon center are accessed without the usage of base. Control and deuterium-labeling experiments have been investigated to probe into the reaction mechanism.
View Article and Find Full Text PDFStereoselective Copper-Catalyzed Cross-Coupling of α-CF-Allylboronic Acids with Diazoketones.
J Org Chem
January 2025
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
We have studied copper-catalyzed cross-coupling of chiral α-CF-substituted allylboronic acids with α-diazoketones. The reaction proceeds with excellent regioselectivity and stereoselectivity via allylic rearrangement. The method is useful for formation a new allylic C(sp)-C(sp) bond with high selectivity.
View Article and Find Full Text PDFRegioselective Cu-Catalyzed Hydrosilylation of Internal Aryl Alkynes.
Org Lett
January 2025
Department of Chemistry, University of Tennessee, Knoxville, Knoxville, Tennessee 37996, United States.
Construction of vinylsilane building blocks is important for advancing the synthesis of complex small molecules and natural products. Herein, we report a highly regio- and stereoselective copper-catalyzed hydrosilylation of unsymmetrical internal aryl alkynes. The reaction is performed across a broad scope of internal aryl alkynes, providing exclusive access to α-vinylsilane alkenyl arene products, including several silylated small molecule drug analogs.
View Article and Find Full Text PDFIn this study, we investigated the ability of -quinone methide (-QM), an electron-poor diene, to undergo inverse electron-demand Diels-Alder (iEDDA) reaction with electron-rich dienophiles, resulting in fused-ring flavonoid systems. In addition, we explored the Michael-type addition using -QM and various nucleophiles, providing access to diarylmethane products. The cycloaddition reactions proceeded in a highly regioselective way, depending on the charge distribution of the reacting partners.
View Article and Find Full Text PDFOnline extraction-LC-MS/MS is an alternative imaging tool for spatial-resolved metabolomics: Mint leaf as a pilot study.
Food Chem
January 2025
Modern Research Center for Traditional Chinese Medicine, Beijing Research Institute of Chinese Medicine, Beijing University of Chinese Medicine, Beijing 102401, China,. Electronic address:
An attempt was made here to a complemental analytical tool for classical MSI approach. OLE-LC-MS/MS imaging was proposed to plot the spatial-resolved metabolome through deploying mint leaf as a proof-of-concept. A dried leaf underwent chemical composition characterization using OLE-LC-Qtof-MS.
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!