ORGN 540 |
| A fluorous phase, Pummerer cyclative–capture strategy allows rapid access to tagged, heterocyclic frameworks. The glyoxamide moiety in substrates (1) acts as a 'trigger' that, when attacked by fluorous thiol (2), captures the fluorous phase tag (RF) in a facile Pummerer cyclization thereby embedding the tag in the framework of the heterocycle (3). Thus, in one step, the fluorous phase tag is introduced and the heterocyclic ring system is built. Convenient modification of the fluorous, heterocyclic scaffolds using a variety of approaches including Pd-catalyzed cross-couplings is possible. Traceless, reductive cleavage of the fluorous phase tag completes a strategy for the high-throughput, fluorous phase synthesis of N-heterocycles. Alternative cleavage strategies that allow additional diversity to be introduced during the removal of the fluorous tag have also been developed.
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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
Division of Organic Chemistry |
