An expeditious synthesis of 4-fluoropiperidines via aza-Prins cyclization |
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| Authors: | J.S. Yadav B.V. Subba Reddy G.G.K.S. Narayana Kumar |
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| Affiliation: | a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
b Université de Rennes 1, Laboratoire CPM, CNRS UMR 6510, Avenue du Général Leclerc, 35042 Rennes Cedex, France |
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| Abstract: | The reaction of aldehydes with N-tosyl homoallylamine in the presence of a solution of tetrafluoroboric acid-diethyl ether complex in dichloromethane at ambient temperature gave the 4-fluoropiperidines in good yields and with high cis-selectivity. This aza-Prins-type cyclization has a wide scope and the use of HBF4·OEt2 makes this procedure simple, convenient, and cost-effective for the preparation of 4-fluoropiperidines. |
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| Keywords: | Aza-Prins cyclization Tetrafluoroboric acid Homoallylic amines 4-Fluoropiperidines |
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