Highly diastereoselective cycloaddition of diarylnitrilimines to the C˭S bond of (1R)-thiocamphor as a source of chiral spiro-1,3,4-thiadiazoles

Abstract

Highly diastereoselective 1,3-dipolar cycloaddition of in situ generated C,N-diaryl nitrilimines to (1R)-thiocamphor leads to chiral spiro-1,3,4-thiadiazolocamphane derivatives in good yields. The structures and stereochemistries of the new cycloadducts were fully established by spectroscopic methods including X-ray diffraction data. The diastereoselectivity observed in this reaction was explained by means of a brief theoretical study.

Keywords:

• C,N-diaryl nitrilimines
• (1R)-thiocamphor
• spiro-1,3,4-thiadiazoles
• diastereoselectivity
• X-ray analysis
• DFT calculations