Abstract
Enantiomeric dilactones ((1R,4R)-(+)-1 and (1S,4S)-(-)-1) of αα′-dihydroxy-αα′-di-tert-butylglutaric acid have been prepared. The Cotton effect sign of the n→π*-transition of the lactone chromophore in enantiomers1 is determined by the contribution of the uncompensated bonds of the δ-dilactone ring, but not by that of the γ-monolactone ring of1. The correlation of the Cotton effect sign of the n→π*-transition with the chirality of the cage structure and the absolute configuration for the series of 1,4-dialkyldilactones of type1 has been suggested. The contribution of the pseudo-a-oriented amide group to, the Cotton effect sign of the lactone n→π*-transition (the effect of the third chiral sphere) in diastereomeric lactonamides2a,b predominates over that of the nonplanar bonds of the heterocycle (over the effect of the second chiral sphere).
Published Version
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call