Convenient methods for the synthesis of highly functionalized and naturally occurring chiral allenes |
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| Institution: | 1. Department of Pathophysiology, Plant Protection Institute, Centre for Agricultural Research, Hungarian Academy of Sciences, Herman Ottó út 15, H-1022 Budapest, Hungary;2. Ecotoxicology and Environmental Analysis Group, Plant Protection Institute, Centre for Agricultural Research, Hungarian Academy of Sciences, Herman Ottó út 15, H-1022 Budapest, Hungary;3. Department of Entomology, Faculty of Horticultural Science, Corvinus University of Budapest, H-1118 Ménesi út, 44, H-1118 Budapest, Hungary;4. Institute of Biochemistry, Biological Research Centre, Hungarian Academy of Sciences, Temesvári krt. 62, H-6726 Szeged, Hungary;1. Entomology Department, Faculty of Science, Ain Shams University, Cairo, Egypt;2. Entomology Department, Faculty of Science, Benha University, Al-kalyobya, Egypt;3. Biology Department, Faculty of Science, King Khalid University, Abha, Saudi Arabia;1. Laboratory of Glyco-organic Chemistry, The Noguchi Institute, 1-8-1, Kaga, Itabashi-ku, Tokyo 173-0003, Japan;2. Department of Nanobiology, Graduate School of Advanced Integration Science, Chiba University, 648, Matsudo, Matsudo, Chiba, 271-8510, Japan;1. M.V. Lomonosov Moscow State University, Physics Department, 119991, GSP-1, Moscow, Russia;2. M.V. Lomonosov Moscow State University, Chemistry Department, 119991, GSP-1, Moscow, Russia;3. National Research Center “Kurchatov Institute”, Moscow 123182, Russia;4. National Nuclear Research University “Moscow Engineering Physics Institute (MEPhI)”, Moscow 115409, Russia;1. Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan;2. South Ehime Fisheries Research Center, 1289-1 Funakoshi, Ainan, Ehime 798-4292, Japan;3. Integrated Center for Sciences, Tarumi Station, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan |
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| Abstract: | A convenient two step procedure to access highly functionalized chiral allenes using chiral N-methylcamphanyl piperazine derivatives is described. In this transformation, chiral propargylamines are obtained in 79–96% yields with up to 99:1 dr by the CuBr catalyzed reactions of chiral piperazine derivatives with 1-alkynes and aldehydes containing functional groups, which are converted into chiral allenes in the presence of zinc bromide, affording the chiral allenes in 59–85% yields and with up to 99% ee. The antifungal agent Sapium japonicum and an allene precursor intermediate for the synthesis of the pheromone of the male dried bean beetle 15 are obtained in 72–78% yields and with up to 98% ee following this methodology. |
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