ORGN 652 |
Tandem [4+2] cycloaddition / [3,3] sigmatropic rearrangement strategy for highly diastereoselective synthesis of nitro decalins
| Peter A. Wade and S. Manikandan. College of Arts and Sciences, Department of Chemistry, Drexel University, Philadelphia, PA 19104 |
| Tandem reactions are synthetically efficient protocols for the rapid introduction of molecular complexity. Nitronic esters are important synthetic precursors for heterocyclic derivatives. In continuation of our efforts to explore the synthetic versatility of novel nitronic esters, we wish to disclose a highly diastereoselective synthesis of 1-nitro decalins. In the presence of SnCl4, 1-(α-styryl) cyclohexene and trans β-nitro styrene underwent hetero Diels-Alder reaction affording cyclic nitronic ester. The nitronic ester underwent facile [3,3] sigmatropic rearrangement at room temperature to afford a 97:3 diastereomeric mixture of nitro decalin derivatives. Full details of this new tandem [4+2] cycloaddition / [3,3] sigmatropic rearrangement reaction will be presented. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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