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http://dx.doi.org/10.1021/jo951163m | DOI Listing |
J Org Chem
February 2024
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P.R. China.
A practical and efficient protocol for synthesis of >99% diastereopure - and -alkenyl nitriles is developed, through tetramethylthiourea-mediated stereospecific deoxygenation of respective - and -cyanoepoxides in ethanol. The desired products are obtained in excellent yields.
View Article and Find Full Text PDFNat Commun
November 2023
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P.R. China.
Recently, the asymmetric bifunctionalization of alkenes has received much attention. However, the development of enantioselective alkoxyalkenylation has posed a considerable challenge and has lagged largely behind. Herein, we report a new palladium-catalyzed enantioselective alkoxyalkenylation reaction, using a range of primary, secondary, and tertiary γ-hydroxy-alkenes with alkenyl halides.
View Article and Find Full Text PDFMolecules
October 2023
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China.
Selective dehydrogenative silylation is one of the most valuable tools for synthesizing organosilicon compounds. In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was firstly developed to access ()-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance. Furthermore, two pathways for RuH(CO)(PPh)/NBE-catalyzed dehydrogenative intermolecular silylation of alcohols and alkenes as well as intermolecular silylation of naphthol derivatives were investigated with HSiEt as the hydrosilane reagent.
View Article and Find Full Text PDFJ Org Chem
February 2023
School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, U.K.
Fluorescent unnatural α-amino acids are widely used as probes in chemical biology and medicinal chemistry. While a variety of structural classes have been developed, there is still a requirement for new environmentally sensitive analogues that can closely mimic proteinogenic α-amino acids. Here, we report the synthesis and fluorescent properties of highly conjugated, benzotriazole-derived α-amino acids designed to mimic l-tryptophan.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
June 2022
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
Allylic gem-dichlorides are shown to be efficient substrates for catalytic asymmetric allylboration of alkynes. The method employs a chiral NHC-Cu catalyst capable of generating in a single step chiral skipped dienes bearing a Z-alkenyl chloride, a trisubstituted E-alkenyl boronate and a bis-allylic stereocenter with excellent levels of chemo-, regio- enantio- and diastereoselectivity. This high degree of functionalization makes these products versatile building blocks as illustrated with the synthesis of several optically active compounds.
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