Efficient synthesis of chiral Δ2-1,3,4-thiadiazolines from α-pinene and verbenone

Abstract

The synthesis of chiral cyclobutane 1,3,4-thiadiazoline derivatives starting from (-)alfa pinene and (-)verbenone was studied. The diastereoisomeric excesses of the products obtained depended strongly upon the starting chiral ketone. The stereochemical assignments of the synthesized compounds were performed by NMR spectroscopy, X-ray analysis, and theoretical calculations.