Direct synthesis of methyl 2-diazo-4-aryl-3-butenoates and their application to the enantioselective synthesis of 4-aryl-4-(1-naphthyl)-2-butenoates |
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| Affiliation: | 1. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong;2. Department of Chemistry, Faculty of Science, Kyoto University, Japan;1. NIH Chemical Genomics Center, Division of Preclinical Innovation, National Center for Advancing Translational Sciences, National Institutes of Health, Bethesda, MD 20892, United States;2. Department of Structural and Chemical Biology, Icahn School of Medicine at Mount Sinai, New York, NY, United States;3. Allen and Frances Adler Laboratory of Blood and Vascular Biology, Rockefeller University, New York, NY, United States;4. Proteomics Resource Center, Rockefeller University, New York, NY, United States;5. Touro College of Pharmacy, New York, NY, United States;6. Ekam Imaging, Boston, MA, United States;1. Department of Bio-Health Technology, Kangwon National University, Chuncheon 200-701, Republic of Korea;2. Institute of Bioscience and Biotechnology, Kangwon National University, Chuncheon 200-701, Republic of Korea;1. Department of Medical Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Science, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China;2. Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China |
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| Abstract: | An improved one-flask synthesis of various methyl 2-diazo-4-aryl and 4-heteroaryl-3-butenoates, precursors to donor/acceptor substituted carbenoids, is described. Their Rh2(S-DOSP)4 catalyzed reaction with 1-acetoxy-3,4-dihydronaphthalene, via a combined C–H activation/Cope rearrangement pathway followed by elimination of acetic acid affords a highly enantioselective (98–99% ee) entry to methyl 4-aryl- and 4-heteroaryl-4-(1-naphthyl)-2-butenoates. |
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