ORGN 168 |
| In recent years boron-containing building blocks have emerged as one of the most attractive starting materials in various organic transformations notably due their high stability, ease of availability and low toxicity. But there are very few reports available on 2-boron substituted 1,3-dienyl derivatives and corresponding Diels-Alder cycloaddition chemistry presumably due to their high propensity towards dimerization. We for the first time have prepared 1,3-dienyl-2-trifluoroborates and demonstrated their ability to participate in tandem Diels-Alder/cross-coupling reactions under mild conditions. The present report will describe the synthesis of representative 4-substituted alkyl and aryl dienyl boron compounds using halogen magnesium exchange reactions at room temperature as well as their reactivities in the above-mentioned methodology. We will also present rhodium-catalyzed tandem Diels-Alder/hydrolysis reactions and their preferential mode of stereoselectivity. The success of the latter methodology could be very useful for the construction of biologically significant core structures in the cis clerodane type terpenes.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |