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Both N-phthaloyl aminoacid amides and methyl amides as well as N-phthaloyl dipeptide methyl esters give Cotton effects of opposite signs at around 220 and 240nm. The signs of these Cotton effects are directly correlated with the absolute configuration of the N-phthaloyl substituted stereogenic center: for l-configuration the Cotton effect at 240nm is positive and the Cotton effect at 220 is negative...
Absolute configurations of C(α)-chiral primary allylic amines can be determined from the CD spectra of their N-phthaloyl derivatives. This method is based on the exciton coupling of the allowed π-π* transitions in the phthalimide and olefin chromophores: positive helicity of the N-C α -C C bond system results in a positive Cotton effect at ca. 220 nm, a negative Cotton effect is obtained...
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