Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones |
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| Affiliation: | 1. Departamento de Quı́mica Orgánica (C-I), Universidad Autónoma, 28049 Madrid, Spain;2. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK;1. Centre for Commercialization of Regenerative Medicine, Toronto, ON, M5G 1M1, Canada;2. Australian Institute for Bioengineering and Nanotechnology, Building 75, Corner College and Cooper Roads, The University of Queensland, St Lucia 4067 QLD, Australia;1. Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China;2. School of Chemistry and Pharmacy, University of East Anglia, Norwich Research Park, Norwich, Norfolk NR4 7TJ, UK;3. College of Materials Science and Opto-Electronic Technology, University of Chinese Academy of Sciences, Beijing 100190, China;1. Laser & Fiber Electronics Group, Faculty of Electronics, Wroclaw University of Science and Technology, 50-370, Wroclaw, Poland;2. Department of Electrical Engineering, Princeton University, Princeton, NJ, 08544, USA;1. Guilan Regional Electric Company, Rasht, Iran;2. Department of Electrical Engineering, Faculty of Engineering, University of Guilan, Rasht, Iran |
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| Abstract: | We describe the addition reactions of α-thiocarbanions derived from sulfoxides, thioethers, and sulfones to 2-(p-tolylsulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the substrate, but it is modulated by the nature of the sulfur function at the reagent (SOTol>SO2Ph>SPh). The highly stereoselective formation of the second stereogenic center generated in these reactions from prochiral anions is only achieved with sulfinylcarbanions, the configuration of which controls that of such a center. |
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