期刊
TETRAHEDRON LETTERS
卷 58, 期 5, 页码 470-473出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.12.061
关键词
1,2,5,6-Tetrahydropyridine; Piperidine; Stereoselective; Propargylamine; Azaheterocycle
资金
- Berry College
- Kirbo Scholars Program
A general approach for the stereoselective synthesis of 2-substituted 1,2,5,6-tetrahydropyridines and piperidines is described. The addition of 4-chloro-1-butyne to Ellman sulfinimines to produce chloro-containing propargylamines, reduction with Lindlar catalyst, and cyclization using LHMDS provides efficient, stereoselective access to diverse 2-substituted 1,2,5,6-tetrahydropyridines. For substrates incompatible with the LHMDS cyclization reaction conditions removal of the sulfinamide moiety and cyclization with Cs2CO3 allows the preparation of the corresponding 2-substituted 1,2,5,6-tetrahydropyridines. This method can be extended to the synthesis of 2-substituted piperidines through reduction of the chloro-containing propargylamine with PtO2. (C) 2016 Elsevier Ltd. All rights reserved.
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