Formation of δ-Lactones by Cyanide Catalyzed Rearrangement of α-Hydroxy-β-oxoesters
David Kieslich1, Jens Christoffers1
1Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Str. 9-11, D-26111 Oldenburg, Germany.
Abstract:
δ-Valerolactone derivatives are formed by cyanide-catalyzed ring-transformation of cyclic α-hydroxy-β-oxoesters. This unprecedented reaction defines a new synthetic methodology, and the products are obtained in up to quantitative yields. Several alkyl substitutions as well as different ester residues are tolerated. Furthermore, benzo- and heteroarene-annulated starting materials are converted without problems. As an additional benefit, the starting materials are straightforwardly accessed by cerium-catalyzed aerobic α-hydroxylation of readily available β-oxoesters.
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