Committee ChairBates, Robert B.
MetadataShow full item record
PublisherThe University of Arizona.
RightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
AbstractDianions were made for the first time from α-ketoacids, using n-BuLi/t-BuOK (Lochmann's base), and alkylated on oxygen with dialkyl sulfates, alkyl sulfonates (triflates, tosylates), or alkyl halides to produce α-alkoxyacrylic acids. This is a more direct and efficient route to these acids than those used earlier. The α -ketoacids used were pyruvic acid, 2-oxobutanoic acid, and 3-methyl-2-oxobutanoic acid. 2-Oxobutanoic acid gave (Z)-2-alkoxy-2-butenoic acids with very high stereoselectivity. 3-Methyl-2-oxobutanoic acid gave 3-methyl-2-alkoxy-2-butenoic acids in low yields, but this is the only route to these acids to date.