Catalytic asymmetric syntheses. : Part III. Asymmetric hydrogenation of piperitenone catalysed by chiral ruthenium hydrides : An example of a catalytic kinetic resolution1 |
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| Institution: | 1. Normandie Univ., ENSICAEN, UNICAEN, CNRS, LCS, 14000, Caen, France;2. Chemistry Department, St. John Fisher College, 3690 East Avenue, Rochester, NY 14618, USA;3. Instituto de Tecnología Química, Universitat Politècnica de Valencia – Consejo Superior de Investigaciones Científicas (UPV-CSIC), Avda. de los Naranjos s/n, 46022, Valencia, Spain;1. Centre of Physics of University of Minho and Porto (CF-UM-UP), Campus de Gualtar, 4710-057 Braga, Portugal;2. University of Minho, CMEMS—UMINHO, Campus de Azurem, 4804-533 Guimaraes, Portugal;3. Department of Quantum Technologies, Wroclaw University of Science and Technology, Wroclaw 50-370, Poland;4. Dept. of Materials Science and Metallurgy, 27 Charles Babbage Rd., Cambridge CB3 OFS, UK;5. Department of Materials, Imperial College London, Exhibition Road, London SW7 2AZ, UK;1. Prince Sultan Research Chair for Environment and Wildlife, Department of Botany & Microbiology, College of Sciences, King Saud University (KSU), Riyadh, Saudi Arabia;2. Research Department of Chemistry, Nehru Memorial College (Affiliated to Bharathidasan University), Puthanampatti 621007, Tiruchirappalli District, Tamil Nadu, India;3. Department of Medical Laboratory Sciences, College of Medicine and Health Sciences, ArbaMinch University, Arba Minch, Ethiopia;1. SP Technical Research Institute of Sweden, SP Process Development, Box 5607, SE-114 86, Stockholm, Sweden;2. Department of Biosciences and Nutrition, Karolinska Institute, SE 141 57, Huddinge, Sweden |
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| Abstract: | Piperitenone has been hydrogenated in the presence of chiral ruthenium catalysts to give piperitone, menthone and isomenthone. Starting from piperitone (42 % e.e.) excellent selectivity (⋍80 % e.e.) was obtained with menthone. The mechanism of the reaction, a double asymmetric synthesis, is discussed with respect to kinetic resolution of piperitone as well as the effect of the chiral center in the substrate on the catalytic asymmetric induction. |
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