Diastereoselective synthesis of (E)-1-trimethylsilyl-3-en-1-ynes by palladium-catalyzed cross-coupling reaction between trimethylsilylethynylzinc chloride and stereoisomeric mixtures of 1-bromo-1-alkenes |
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| Affiliation: | 1. Department of Chemistry, Duke University, Durham, NC 27708, United States;2. Department of Chemistry, The Catholic University of Korea, Bucheon 14662, Republic of Korea;3. Korea Research Institute of Bioscience and Biotechnology, Daejeon 34141, Republic of Korea;1. N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991 Moscow, Russian Federation;2. The Higher Chemical College of the Russian Academy of Sciences, Miusskaya Pl. 9, 125047 Moscow, Russian Federation;1. Graduate School of Life Science, Hokkaido University, N21W11, Kita-ku, Sapporo 001-0021, Japan;2. Medicinal Chemistry Pharmaceuticals, Co. Ltd., N21W10, Kita-ku, Sapporo 001-0021, Japan;1. Istituto di Chimica Biomolecolare – CNR, Trav. La Crucca 3, 07100 Sassari, Italy;2. Dipartimento di Chimica e Biologia – Università di Salerno, via Ponte Don Melillo, 84084 Fisciano Salerno, Italy;1. Department of Chemistry, Panjab University, Sector 14, Chandigarh 160014, India;2. Department of Chemistry, DAV College, Sector 10, Chandigarh 160011, India;3. Institut für Anorganische Chemie, Technische Universität Bergakademie, Freiberg, 09596 Freiberg, Germany |
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| Abstract: | In the stereospecific palladium-catalyzed cross-coupling reaction of triimethylsilyl-ethynylzinc chloride, (B)-1-bromo-1-alkenes react preferentially in the presence of the corresponding (Z)-stereoisomers. |
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