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Selective reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with alkyl primary amines: application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones |
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| Authors: | Te-Fang Yang Chien-Hung Shen Li-Hsun Chen |
| Affiliation: | a Department of Applied Chemistry, National Chi Nan University, Puli, 545, Nantou, Taiwan b Department of Applied Chemistry, Chaoyang University of Technology, Wufong, 413, Taichung, Taiwan |
| Abstract: | Reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with various alkyl primary amines gave regio- and stereo-specific [3.2.1]bicyclic α-amino ketones. A detailed mechanism of the reaction was discussed. This reaction was further applied to the preparation of some camphor-derived oxazaborolidines, one of which proved to be an efficient chiral catalyst for the asymmetric borane reduction of prochiral aryl ketones at room temperature. |
| Keywords: | Ring expansion Bicyclic amino ketone Chiral catalyst Asymmetric reduction of ketone |
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