Synthesis and Structural Characterization of Novel Camphor-derived Amines |
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Authors: | Grošelj Uroš Sevšek Alen Ričko Sebastijan Golobič Amalija Svete Jurij Stanovnik Branko |
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Affiliation: | Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana, Slovenia. |
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Abstract: | Two novel 4‐substituted camphidine derivatives 10a , b have been prepared from (+)‐camphor ( 1 ) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b , formed as a side product during the hydrogenation of arylidene ketone 3b , under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12 . (1S)‐(+)‐Camphorquinone ( 13 ) was transformed into diamines 15 and 16 in two steps, the former being cyclized into an imidazoline salt 17 , an N‐heterocyclic carbene precursor. The structures of all novel compounds have been meticulously characterized using NMR techniques and/or single crystal X‐ray analysis. Chirality 24:778–788, 2012. © 2012 Wiley Periodicals, Inc. |
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Keywords: | camphor enaminone methodology Beckmann rearrangement camphor‐derived amines NHC ligand precursor |
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