[Stereochemistry of proton catalyzed dimerization of 3-alkyl-indoles].
Two dimers (I and II) having 3,3'-disubstituted 2-(2'-indolil)-indoline skeleton were prepared by trifluoroacaetic acid treatment of N-acetyl-L-tryptophan methyl ester. Their CD spectra suggest enantiomeric configuration in 2- and 3-positions of indoline ring. The (-)-enantiomer of skatole dimer has nearly the same CD spectrum as the dimer I. X-ray crystal structure determination of (-)-skatole dimer shows, that it has 2S,3S-trans configuration in the indoline ring suggesting the same configuration of dimer I and opposite, 2R,3R-trans configuration of dimer II.
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D018360:Crystallography, X-Ray; D019281:Dimerization; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011522:Protons; D012862:Skatole / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D011522:Protons; D012862:Skatole