ORGN 826 |
| In the last decade, organic chemists have paid much attention to the ring expansion of [2.2.1]bicyclic carbinols due to its potential application to the preparation of precursors of natural products. Herein, we report that camphor- and camphene-derived formyl[2.2.1]bicyclic carbinols reacted with primary alkyl/aryl amines (RNH2: R = Me, Et, Ph, Bn, etc.) to form the corresponding imino[2.2.1]bicyclic carbinols in dichloromethane at room temperature. After the imono[2.2.1]bicyclic carbinols were refluxed in toluene, the [3.2.1]bicyclic α-amino ketones were produced. Especially, the reaction of formyl borneol with aniline and para-substituted anilines in dichloromethane gave directly the [3.2.1]bicyclic products without heating. It is noteworthy that the ring expansion reaction turned out to be one-pot, stereoselective and regioselective. A mechanism of the reaction is to be illustrated. |
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Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |