A convenient method for the preparation of oxazaborolidine catalyst in situ using (S)-α,α-diphenylpyrrolidinemethanol,tetrabutylammonium borohydride,and methyl iodide for the asymmetric reduction of prochiral ketones |
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| Affiliation: | 1. Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, PR China;2. Department of Chemistry and Materials, Yulin Normal University, Yulin 537000, PR China;1. Behbahan Khatam Alanbia University of Technology, Behbahan, Iran;2. School of Chemical Engineering, University of Tehran, Tehran, Iran;1. Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukaramah 715, Saudi Arabia;2. Chemistry Department, Faculty of Science, Cairo University, Giza 12613, Egypt;1. Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Sciences, Tianjin University, Tianjin 300354, PR China;2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300354, PR China;3. National Demonstration Center for Experimental Chemistry & Chemical Engineering Education, Tianjin 300354, PR China;4. National Virtual Simulation Experimental Teaching Center for Chemistry & Chemical Engineering Education, Tianjin University, Tianjin 300354, PR China;5. School of Science, Tianjin Chengjian University, Tianjin 300384, PR China;1. Institute of Materia Medica, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, PR China;2. School of Medicine, Ningbo University, Ningbo 315211, PR China |
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| Abstract: | An oxazaborolidine catalyst is readily prepared in situ at 25 °C in THF using (S)-α,α-diphenylpyrrolidinemethanol and borane generated from tetrabutylammonium borohydride/CH3I reagent system. The oxazaborolidine/BH3 reagent system prepared in this way is useful for the reduction of prochiral ketones to the corresponding alcohols with up to 99% ee. |
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