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Substitution of the β-halogen atoms in methyl (1R,3S)-2,2-dichloro-3-methylycyclopropanecarboxylate with sodium thiophenolate leads to the di(phenylthio) ester (1RS,3S)-4 as a mixture of diastereomers. The cis-trans isomerisation of methyl (1RS,3S)-3-methyl-2,2-bis(phenylthio)cyclopropanecarboxylate 4, basic hydrolysis and subsequent crystallization gave the corresponding acid (1R,3S)-5 in high diastereomeric and enantiomeric purity. On the other hand, ring opening of the ester (1RS,3S)-4 under acidic conditions leads to methyl 3-methyl-4,4di(phenylthio)prop-3-enoate (8) or the chiral S-phenyl thioester methyl (3S)-3-methyl-4-oxo-4(phenylthio)butanoate (7).

Chiral methyl trans-2,2-dichloro-3-methylcyclopropanecarboxylate upon exposure to thiophenolate nucleophile