ORGN 639 |
| An efficient and direct three component Strecker reaction using ketones were not so far attained. Quite often either stepwise reaction or use of high pressure is required. Application of gallium(III) triflate as stable, environmentally more benign, and reusable Lewis acid catalysts for various organic synthetic transformations has been recently explored in our laboratories. We found that gallium(III) triflate is an effective catalyst for the synthesis of α-aminonitriles from not only aldehydes but ketones under mild conditions. Various fluorinated aldehydes and ketones with various amines and trimethylsilyl cyanide afford the corresponding fluorinated α-aminonitriles in high yields. These fluorinated α-aminonitriles can be easily converted to fluorinated α-aminoacids which are known to have significant biological properties. The reactions are simple, clean and catalytically very efficient (only 5% catalyst is required in most cases). The use of many other metal triflates for Strecker reactions using ketones and their fluorinated analogs will be discussed.
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New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
