A convenient access to chiral and racemic (Z)-1-bromo-3-benzoxy-1-butene |
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| Institution: | 1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;2. School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, China;3. Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, China;1. Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-8628, Japan;2. Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8, Kita-Ku, Sapporo 060-8628, Japan;1. Faculty of Chemistry, Opole University, Ul. Oleska 48, 45-052 Opole, Poland;2. Department of Bioorganic Chemistry, Faculty of Chemistry, Wroc?aw University of Technology, Wybrze?e Wyspiańskiego 27, 50-370 Wroc?aw, Poland |
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| Abstract: | The conversion of propargylic trimethylsilyl ether 3 into (Z)-1-bromo-3-benzoxy-1-butène 1 was achieved by hydroboration with pinacolborane followed by successive treatment with bromine and DBU. The key step of the chiral synthesis involves the asymmetric reduction of the α,β-unsaturated ketone 7 with (?)-diisopinocampheylchloroborane (?)-Ipc2BCl]. |
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