Journal
TETRAHEDRON LETTERS
Volume 50, Issue 11, Pages 1199-1202Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.12.101
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- University of Sydney
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The oxidation of N-phenyltetrahydroisoquinolines occurs rapidly with DDQ. Under ambient conditions and in the presence of nitromethane, the corresponding beta-nitroamine derivatives are isolated in good to excellent yields. Variation in the electronic nature of the isoquinoline and the N-phenyl substituent showed that a broad range of substituents are tolerated, with electronic communication between the isocluinoline aromatic ring and the C1 carbon being stronger than with the N-aryl ring. Reduction of the beta-nitroamines to the corresponding novel chiral vicinal diamines are straightforward, Examination of the reaction by H-1 NMR spectroscopy suggested that the reaction proceeds via an iminium ion, which then reacts with nitromethane upon work-up. This information was used to shorten the required reaction time. (C) 2009 Elsevier Ltd. All rights reserved.
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