ORGN 461 |
| We have recently developed a number of variations of a three-component reaction between amines, carbonyl compounds and organoboron derivatives. Although this process works well with a variety of organoboron compounds, the use of alkynyl boronic acids and boronates was hampered by their facile decomposition. Herein, we report that this type of three-component process takes place readily with potassium alkynyl trifluoroborates, which are air and water stable and can be used effectively in the presence of a Lewis acid catalyst. This method was employed in the synthesis of a variety of functionalized N-substituted propargylic amines as well as several related amino alcohols and heterocycles, such as piperazin-2-ones. Additional related transformations of alkynyl trifluoroborates will also be reported. |
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Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |