Journal
TETRAHEDRON LETTERS
Volume 53, Issue 42, Pages 5707-5710Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.08.062
Keywords
Nitro-Mannich; Tetrahydroquinoline; Diastereoselective; Cyclisation; Heterocycle
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Funding
- EPSRC
- GSK
- Ministerio de Educacion (Spain)
- Engineering and Physical Sciences Research Council [EP/F068344/2] Funding Source: researchfish
- EPSRC [EP/F068344/2] Funding Source: UKRI
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A simple protocol for the diastereoselective synthesis of 3-nitrotetrahydroquinolines has been developed using an intramolecular nitro-Mannich reaction. In situ formation of an imine generated from treatment of 2-(2-nitroethyl)phenylamine with an aldehyde, in EtOH at room temperature, and subsequent addition of NH4OH, led to the formation of trans-products in high yield and diastereoselectivity for 15 representative examples. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.
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