ORGN 141 |
Synthesis of chiral tetrahydrofuranones, tetrahydrothiophenones, and azetidinones via rhodium (II)-catalyzed cyclization reactions
| Lindsay Odom, Young B. Kim, and John M. Rimoldi. Department of Medicinal Chemistry, University of Mississippi, Laboratory for Applied Drug Design and Synthesis, University, MS 38677 |
| Rhodium (II)-catalyzed cyclization reactions of N-protected α-amino diazoketones generally afford 4- and 5-membered ring heterocyclic systems, with product formation influenced by the nature of both the N- and X-protecting groups. We have exploited the use of an X-tert-butyl protecting group (X = O, S) that, after initial formation of the oxonium or sulfonium ylide from the rhodium (II) catalyzed reaction, decomposes to isobutylene and the respective tetrahydrofuranones and tetrahydrothiophenones. The effect of N-protecting group, solvent, and temperature on the product yields, preference to N- vs O-insertion, and enantiomeric purity 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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