ORGN 160 |
Regioselective Suzuki coupling reactions on pyrroles: Studies and applications
| Scott T Handy, Yanan Zhang, Jesse J Sabatini, and Inessa Vulfova. Department of Chemistry, SUNY Binghamton, Binghamton, NY 13902 |
| In the total synthesis of Lamellarin G trimethyl ether, our group has successfully constructed the Lamellarin core using a series of sequential, regiocontrolled halogenation/Suzuki cross-coupling reactions to completely functionalize a simple pyrrole ester. In an effort to develop an even more concise route to tri- and tetrasubstituted pyrroles, the regioselective coupling of dihalopyrroles has been investigated. In particular, the electronic and steric influences upon the regioselectivity of the Suzuki coupling of 4,5-, 3,4-, and 3,5-dibromopyrrole esters and 4,5-dihalopyrrole aldehydes have been examined. Variations in the conditions used for the Suzuki coupling reaction have led to further improvements in the inherent selectivity observed in these reactions. Finally, initial efforts have shown that not only can regioselectivity be achieved, but that two couplings can actually be carried out in a sequential, one-pot method. The results of these studies and synthetic applications will be presented. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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