ORGN 107 |
| 1,3-Dipolar cycloaddition reactions are fundamental processes in organic chemistry and offer an efficient and reliable synthetic methodology to access five-membered heterocycles, an important building block that forms the basic frame work of many natural products. Herein we report [2+3] annulation of thiomethylacrylate 1 and azomethine ylide precursor 2 towards the synthesis of novel 3-methylsulfanyl-pyrrolidines 4. Alternatively, we have also explored the alkylation of 5 with dimethyldisulfide/LDA for the introduction of thiomethyl group towards the synthesis of 3-methylsulfanyl-pyrrolidines 4 in moderate to good yields. Efficacy of these two routes under various conditions/catalysts and the resolution of 3-methylsulfanyl-pyrrolidines will be presented.
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Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster
Division of Organic Chemistry |
