ORGN 482 |
| The synthesis of amine derivatives containing the allenyl or propargylic moiety often requires multi-step synthetic strategies. Herein we present our studies on a direct route towards these synthetically novel scaffolds through a one step, three-component reaction among an allenyl boron derivative, a carbonyl compound and an amine. This process was employed in the synthesis of a variety of amino acids and amino alcohol derivatives, which were subsequently converted to a number of novel heterocycles. The scope of the three-component process was also extensively investigated, revealing a remarkable sensitivity to the type of product formed based on the particular components used, as well as the reaction conditions. The use of chiral components, including chiral amines, chiral aldehydes and carbohydrates was shown to proceed with excellent stereoselectivity. Further synthetic manipulation of the allenyl products lead directly to different types of heterocyclic systems, including aziridines, piperazines and pyrrolines. Overall, this new and versatile methodology was shown to be synthetically useful for the concise synthesis of multi-functionalized amines and heterocycles. |
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |