Efficient synthesis of chiral D-2-1,3,4-thiadiazolines from a-pinene and verbenone

GABRIELA P. SARMIENTO,A PABLO D. ROUGE,A LUCAS FABIAN,B DANIEL VEGA, C ROSA M. ORTUÑO,D GRACIELA Y. MOLTRASIO,A AND ALBERTINA G. MOGLIONI.

TETRAHEDRON-ASYMMETRY

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2011 vol. 22 p. 1924 - 1929

0957-4166

The synthesis of chiral cyclobutane 1,3,4-thiadiazoline derivatives starting from (-)-a-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.