ORGN 310 |
| Gerardo Torres and José A. Prieto. Department of Chemistry, University of Puerto Rico, PO Box 23346, San Juan, PR 00931-3346 |
| Over the years, our research laboratory has been working on the development of synthetic methodologies for the preparation of polypropionates based on epoxide chemistry. Specifically, we are using the cleavage of 3,4-epoxy alcohols with alkynyl alanes as the key feature for the preparation of polypropionate chains. The cleavage of these epoxides produces the expected 1,3-diol or the unwanted 1,4-diol products with high regioselectivity. Consequently, we have undertaken a 27Al and 13C NMR study on the organoaluminum-epoxide complex. Various 2-methyl-3,4-epoxy alcohols were treated with Et3Al and analyzed by NMR in order to understand the basis of the observed regioselectivity. We also use theoretical ab-initio calculations to study the difference in the systems. We have found that there is a conformational vias associated with the regioselectivity of this reaction. The details of this study will be presented. Supported by NIH RISE (1R25-GM-61151-01A1) and NIH SCORE (2S06GM-08102-29).
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Physical Organic, Combinatorial, Materials, Molecular Recognition
8:00 PM-10:00 PM, Tuesday, March 30, 2004 Anaheim Convention Center -- Hall A, Poster
Sci-Mix
Division of Organic Chemistry |