Stereochemical course of the hydrogen migration in the boron trifluoride etherate-catalyzed rearrangement of 1,1-disubstituted epoxides |
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| Affiliation: | 1. Orekhovich Institute of Biomedical Chemistry, Moscow, Russia;2. Engelhardt Institute of Molecular Biology RAS, Moscow, Russia;1. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012 Ji’nan, Shandong, PR China;2. Department of Pharmacology, School of Medicine, Shandong University, 44 West Culture Road, 250012 Ji’nan, Shandong, PR China;3. Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium;1. Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia;2. J. Heyrovský Institute of Physical Chemistry, v.v.i., Academy of Sciences of the Czech Republic, Dolejškova 3, CZ-182 23 Prague, Czech Republic;3. Department of Physical Chemistry, Institute of Chemical Technology, Technická 5, CZ-166 28 Prague, Czech Republic;1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich St., 5/2, 220141 Minsk, Belarus;2. Department of Plant Cell Biology and Bioengineering, Biological Faculty, Belarusian State University, Minsk, Belarus;3. University of Chemistry and Technology, Technická 5, CZ-166 28 Praha 6, Czech Republic |
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| Abstract: | Mechanistic studies on the BF3·Et2O-catalyzed rearrangement of optically active, regioselectively deuterated 1,1-disubstituted epoxides to aldehydic products revealed that the two hydrogens migrate at the migration terminus with opposite stereochemical preferences, i.e. the hydrogen anti to the bulky substituent prefers to migrate with inversion of configuration, whereas the hydrogen syn to the bulky substituent prefers to migrate with retention of configuration. |
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