Stereochemistry of proton catalyzed dimerization of 3-alkyl-indoles
Lów, M.
Acta Pharmaceutica Hungarica 69(1): 20-23
1999
ISSN/ISBN: 0001-6659 PMID: 10513408 Document Number: 506537
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.