80922-57-2Relevant academic research and scientific papers
Synthesis of Hydroxy-γ-lactones from α,β-Unsaturated Aldehydes
Marschall, Helga,Penninger, Josef,Weyerstahl, Peter
, p. 49 - 67 (2007/10/02)
According to Scheme 1 the α,β-unsaturated aldehydes 3-9 react in three steps (epoxidation, PO olefination, and selective hydrogenation) to give the epoxy esters 36-42.Generally, these steps are interchangeable, predominantly the epoxidation and olefination.Thus, the epoxy acid esters 26-32 are synthesized via the epoxides 10-16 or via the dienoic esters 17-23.Homogeneously catalyzed hydrogenation of 26-31 gives the saturated esters 36-41.In case this reaction fails (e.g. with 32), sequence e, g (Scheme 1) via γ,δ-unsaturated esters (e.g. 35) might be successful.All these α,β-unsaturated esters 17-23 and 26-32 possess (E) configuration.Even the reaction of 3 or 6 with the propionate 2 leads to the (E) esters 24 or 25, respectively.Hydrolysis of the epoxy acid esters 36-41 gives the hydroxy-γ-lactones 43-48.
