ORGN 142 |
| We have recently reported a MgBr2•OEt2-promoted direct aldol addition of simple thioesters via soft enolization and have shown it to be a mild, simple, and efficient method. Notably, we demonstrated that we can chemoselectively generate thioester enolates using a bulky amine base in the presence of an aldehyde having a single α-proton, giving the aldol products in high yield with only trace aldehyde self-condensation. We have extended this approach to the use of α-halo thioester nucleophiles to obtain either α,β-epoxy thioesters or α-halo-β-hydroxy thioesters, depending on the conditions used. The products of these reactions are particularly versatile synthetic intermediates and can be readily converted into a wide variety of polyfunctionalized compounds.
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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 |
