Composition and structure of activated complexes in stereoselective deprotonation of cyclohexene oxide by a mixed dimer of chiral lithium amide and lithiated imidazole |
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| Affiliation: | 1. Chemistry Department, Faculty of Science, King Abdulaziz University, 80203 Jeddah, Saudi Arabia;2. Chemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt;1. Department of Pharmaceutical Chemistry, University of Debrecen, POB 70, H-410 Debrecen, Hungary;2. Department of Inorganic and Analytical Chemistry, University of Debrecen, POB 21, H-410 Debrecen, Hungary |
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| Abstract: | Stereoselective deprotonation of cyclohexene oxide, using a mixed dimer built of the chiral lithium amide, lithium (1R,2S)-N-methyl-1-phenyl-2-pyrrolidinyl-propanamide, and 2-lithio-1-methylimidazole, has been studied. The composition of the rate limiting activated complex was determined by kinetics to be built from one mixed dimer molecule and one epoxide molecule. Based on this knowledge computational chemistry has been applied to gain insight into possible structures of the activated complexes. |
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