Oxidative cleavage of unsaturated 1,2-diols using chiral lead-tetracarboxylates obtained by in situ metathesis

A combination of an acetate metathesis/cascade transformations process, providing ring enlarged systems decorated with a chiral auxiliary, is presented. The use of a chiral carboxylic acid, such as (S)-2-acetoxypropionic acid, gives diastereomeric mixtures when performed in the racemic series, offering the possibility of a chemical resolution.