Journal
TETRAHEDRON
Volume 78, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131821
Keywords
Piperidine; Nitro-Mannich reaction; Cyclisation; beta-nitroamine; Diastereoselective
Categories
Funding
- Engineering and Physical Sciences Research Council
- China Scholarship Council
- Erasmus scheme
- University College London
- EPSRC [EP/P020410/1] Funding Source: UKRI
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The method synthetizes functionalized piperidines with 3 contiguous stereocentres using diastereoselective nitro-Mannich and reductive cyclization reactions, yielding stereochemically pure products in 19-57% yield.
A method for the synthesis of functionalized piperidines containing 3 contiguous stereocentres in the 2-,3- and 4- positions uses a diastereoselective nitro-Mannich to control stereochemistry. The nitro-Mannich reaction between a beta-aryl/heteroaryl substituted nitroalkanes and glyoxylate imine provides beta-nitro-amines with good selectivity (70:30 to >95:5) for the syn, anti-diastereoisomers. Reductive cyclisation with BF3 center dot OEt2 and Et3SiH gave, after purification, stereochemically pure piperidines in 19-57% yield for ten examples with different 4-aryl/heteroaryl substituents. (C) 2020 Elsevier Ltd. All rights reserved.
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