First enantioselective synthesis of a 1-(trimethylsilyl)alkylamine |
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| Institution: | 1. College of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, Hunan, China;2. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei, China;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;1. Department of Chemistry, Center for Excellence in Molecular Synthesis, University of Science and Technology of China, Hefei, Anhui 230026, P.R. China |
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| Abstract: | Reduction of n-propanoyltrimethylsilane NH-imine with the complex hydride LiBH4/diethyltartrate in THF yielding enantiomerically enriched 1-(trimethylsilyl)butylamine with a 60% enantiomeric excess is the first example of the enantioselective synthesis of such an amine. Other combinations of solvent (ether or THF), hydride (NaBH4 or LiAlH4) and chiral inductor (mono- or diol) failed. |
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