CHIROPTICAL PROPERTIES OF 2-SUBSTITUTED PYRROLIDINES

Article abstract of DOI:10.1016/S0040-4020(01)98926-4

The CD spectra of L-2-methylpyrrolidine, L-prolinol, and their N-methylated derivatives have been determined.As in the 2-substituted piperidines, N-methylation results in an inversion of the sign of the Cotton effects (CE).However, the sign of the long-wavelength CE does not follow the simple helicity rule found for 2-substituted piperidines, since the pyrrolidine ring is itself chiral and makes its own contributions to the observed CE's.The rotational contribution due to pyrrolidine ring chirality appears to be opposite in sign to and larger in magnitude than that due to the 2-substituent in both the secondary and the tertiary amines.