(5S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane: first example of guanidine based in situ recyclable chiral catalytic source for borane-mediated asymmetric reduction of prochiral ketones |
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| Institution: | 1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland;2. Laboratoire d''Electrochimie et de Chimie Physique du Corps Solide, Institute de Chimie-UMR 7177, CNRS, Université de Strasbourg, 4, rue Blaise Pascal, CS 90032, 67081 Strasbourg Cedex, France;1. Institute of Chemistry Timisoara of the Romanian Academy, 24 Mihai Viteazu Blvd., 300223 Timisoara, Romania;2. Institute of Applied Physics, Academy of Sciences of Moldova, 5 Academiei Str., MD–2028 Chisinau, Republic of Moldova;3. Gebze Institute of Technology, Cayirova, 41400 Kocaeli, Turkey;4. National Centre for X-Ray Diffraction, Babes-Bolyai University, Faculty of Chemistry and Chemical Engineering, Department of Chemistry, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania;5. General Inspectorate of Romanian Police, Laboratory of Drug Analysis and Profiling, 40-42 Take Ionescu Blvd., 300042 Timisoara, Romania;6. National Institute for Research and Development in Electrochemistry and Condensed Matter, 144 Dr. A. Paunescu Podeanu Str., 300569 Timisoara, Romania;7. West University of Timisoara, Faculty of Chemistry-Biology-Geography, 16 Pestalozzi Str., 300115 Timisoara, Romania;1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Str. 5, 02660 Kyiv-94, Ukraine;2. Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrs’ka Str. 64, 01033 Kyiv, Ukraine |
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| Abstract: | (5S)-1,3-Diaza-2-imino-3-phenylbicyclo3.3.0]octane has been synthesized and successfully employed, for the first time, as a chiral catalytic source for the borane-mediated asymmetric reduction of prochiral α-halo ketones to provide the corresponding secondary alcohols in high enantiomeric purity. The potential of this guanidine as an in situ recyclable chiral catalytic source for the borane-mediated chiral reduction processes has also been demonstrated. |
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