(S)-(?)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines |
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| Institution: | 1. Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Monash University (Parkville Campus), 381 Royal Parade, Parkville VIC 3052, Australia;2. Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK;1. Zavoisky Physical -Technical Institute of Kazan Scientific Center of Russian Academy of Sciences, Russian Federation;2. Arbuzov Organic and Physical Chemistry Institute of Kazan Scientific Center of Russian Academy of Sciences, Russian Federation;1. Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan;2. Department of Materials Chemistry, Faculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan;1. L.V. Pysarzhevsky Institute of Physical Chemistry of National Academy of Sciences of Ukraine, 31 Nauky avenue, 03028 Kyiv, Ukraine;2. Institute of Chemical Kinetics and Combustion of Siberian Branch of Russian Academy of Sciences, Novosibirsk, Russian Federation;1. Inner Mongolia Key Laboratory of Fine Organic Synthesis, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China;2. Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China |
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| Abstract: | Fluorenylethylchoroformate (FLEC) is a valuable chiral derivatisation reagent that is used for the resolution of a wide variety of chiral amines. Herein, we describe an improved preparation of (S)-(?)-FLEC using an efficient asymmetric catalytic transfer hydrogenation as the key step. We also demonstrate the application of FLEC as a chiral Fmoc equivalent for chiral resolution, with facile deprotection, of tetrahydroquinaldines, and its capacity for inducing regioselective outcomes in nitration reactions. |
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| Keywords: | Fluorenylethylchoroformate Chiral derivatisation Asymmetric transfer hydrogenation Chiral Fmoc Chiral resolution |
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