SYNTHESES OF RACEMIC AND BOTH CHIRAL FORMS OF CYCLOPROPANE-1,2-D(2) AND CYCLOPROPANE-1-C-13-1,2,3-D(3)

The racemic and both chiral forms of cyclopropane-1,2-d2 and cyclopropane-1-C-13-1,2,3-d3 have been prepared efficiently through sequences based on trans-1,2-bis(methoxycarbonyl)cyclopropanes. These diesters have been prepared in racemic form with 1,2-d2 labeling and with 3-C-13-1,2,3-d3 labeling. The labeled diesters have been resolved to provide both chiral forms, and the racemic or resolved diesters have been converted to the corresponding specifically labeled racemic or chiral cyclopropanes through a two-step sequence involving reduction and decarbonylation. The chemical, isotopic, geometrical, and chiral quality of the labeled cyclopropanes in both sets of isomers is estimated to be quite high and strictly comparable.