ORGN 537 |
| Alkene synthesis via the condensation of metalated heteroaryl alkyl sulfones with carbonyl compounds (the modified Julia alkenation) is now a highly valued synthetic method. The intermolecular variant of the modified Julia alkenation has received much attention; however, little is known about corresponding intramolecular processes which should in principle lead to cyclic alkenes. Building on our earlier discovery that ethyl (benzothiazol-2-ylsulfonyl)acetate provides a convenient synthesis of alpha,beta-unsaturated esters from aldehydes under mildly basic conditions, we sought to assess the efficacy of base induced cyclizations of omega-oxoalkyl (benzothiazol-2-ylsulfonyl)acetates (1) as a means to access alpha,beta-unsaturated lactones (2). Results from this ongoing study, which include the development of a generally applicable synthesis of sulfonyl aldehydes 1 and investigation of the dependence of lactone yield and E:Z ratio on ring-size, base, and reaction variables, will be presented.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
