Base-catalyzed diastereodivergent and regioselective domino processes of triketone enones with arylacetaldehydes for the synthesis of tetrahydrofuro[2,3-]furans with four consecutive stereocenters are reported. Good yields and diastereoselectivities are obtained when DBU is employed as a catalyst; in contrast, EtN delivers a different diastereomer in excellent diastereoselectivity. This work offers many advantages, including switchable diastereoselectivity, cheap base catalysts, and a simple operation.
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http://dx.doi.org/10.1021/acs.joc.4c00069 | DOI Listing |
Nat Chem
October 2024
University of Bristol, Bristol, UK.
The selective hetero-dihalogenation of alkenes provides useful building blocks for a broad range of chemical applications. Unlike homo-dihalogenation, selective hetero-dihalogenation reactions, especially fluorohalogenation, are underdeveloped. Current approaches combine an electrophilic halogen source with a nucleophilic halogen source, which necessarily leads to anti-addition, and regioselectivity has only been achieved using highly activated alkenes.
View Article and Find Full Text PDFJ Org Chem
March 2024
Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan,P. R. China.
Base-catalyzed diastereodivergent and regioselective domino processes of triketone enones with arylacetaldehydes for the synthesis of tetrahydrofuro[2,3-]furans with four consecutive stereocenters are reported. Good yields and diastereoselectivities are obtained when DBU is employed as a catalyst; in contrast, EtN delivers a different diastereomer in excellent diastereoselectivity. This work offers many advantages, including switchable diastereoselectivity, cheap base catalysts, and a simple operation.
View Article and Find Full Text PDFChem Sci
February 2022
Department of Chemistry, School of Chemistry and Material Science, Center for Excellence in Molecular Synthesis of CAS, University of Science and Technology of China Hefei 230026 P. R. China
Chem Sci
November 2019
Institut für Chemie , Technische Universität Berlin, Strasse des 17. Juni 115 , 10623 Berlin , Germany . Email:
A copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and ketones allows for the chemo-, regio-, diastereo- and enantioselective assembly of densely functionalized tertiary homoallylic alcohols. The relative configuration of the vicinal stereocenters is controlled by the chiral ligand employed. Subsequent transformations illustrate the versatility of these valuable chiral building blocks.
View Article and Find Full Text PDFNat Commun
June 2019
CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide and Chemical Biology, Ministry of Education; College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, 430079, China.
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