Simple preparation of chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) and applications to asymmetric alkylative esterification |
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| Institution: | 1. Central Research Laboratory, Shiratori Pharmaceutical Co. Ltd, 6-11-24 Tsudanuma, Narashino, Chiba 275-0016, Japan;2. Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan;1. Department of Chemistry, K. J. Somaiya College of Science & Commerce, Mumbai 400077, India;2. Bio-Organic Division, Bhabha Atomic Research Centre, Anushakti Nagar, Mumbai 400094, India;3. Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400 094, India;4. East CHEM School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST Scotland, United Kingdom;1. University of Belgrade, Faculty of Pharmacy, Department of Organic Chemistry, Vojvode Stepe 450, 11221 Belgrade, Serbia;2. University of Belgrade, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Vojvode Stepe 450, 11221 Belgrade, Serbia;1. Moscow State University, Chemical Department, Leninskie Gory 11, Moscow 119991, Russia;2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow 119991, Russia;3. National Research Center “Kurchatov Institute”, Moscow, Russia;4. Peoples'' Friendship University of Russia (RUDN), Moscow, Russia;1. Department of Physics, Fatih University, Büyükçekmece, Istanbul 34500, Turkey;2. Department of Genetics and Bioengineering, Fatih University, Büyükçekmece, Istanbul 34500, Turkey;3. Department of Chemistry, Fatih University, Büyükçekmece, Istanbul 34500, Turkey |
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| Abstract: | New chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) were simply prepared by the action of primary amines on 2-chloro-1,3-dimethylimidazolinium chlorides, derived from the corresponding urea, in high yields. Modest asymmetric induction in alkylative esterification of benzoic acid with (1-bromoethyl)benzene was observed when the 1,3-dimethyl-4,5-diphenyl-2-(1-phenyl- or 1-naphthyl)ethylimino]imidazolidines with all S (or R) configurations were used as bases. |
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