Abstract
Lithium enolates derived from achiral thiol esters react in a highly stereoselective fashion with homochiral aldehydes to yield the corresponding 2-oxetanones. The stereochemical outcome of the reaction corresponds to a non-chelation control. except when O-silylated mandelaldehyde is used. The propiolactones thus formed are efficiently transformed into δ-lactones via Lewis acid promoted dyotropic rearrangements.
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