Journal
CHIRALITY
Volume 24, Issue 10, Pages 789-795Publisher
WILEY-BLACKWELL
DOI: 10.1002/chir.22070
Keywords
electronic circular dichroism; solid-state CD; stereoselective synthesis; TDDFT; chiral synthesis; tetrahydro-b-carbolines
Funding
- Higher Education Commission (HEC), Pakistan
- [TAMOP 4.2.1./B-09/1/KONV-2010-0007]
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The diastereoselective synthesis of optically active 1,3-disubstituted tetrahydro-beta-carbolines using polar protic PictetSpengler cyclization of (S)-tryptophan methyl ester with five aldehydes RCHO (R-CH3, C2H5, C3H7, C4H9, and C6H5) was studied. As an alternate route, the cyclization of (S)-tryptophan with the same aldehydes and subsequent methylation of the resulting tetrahydro-beta-carboline carboxylic acids were also performed for comparison. 13C NMR and electronic circular dichroism (ECD) studies and time-dependent density functional theory ECD calculations data established the relative 1,3 cis/trans and the absolute configuration (1S,3S/ 1R,3S) of the synthesized compounds. The solid-state and solution ECD study of the prepared compounds, supported by ECD calculation and X-ray data, afforded a reliable ECD method for the configurational assignment of 1,3-disubstituted tetrahydro-beta-carbolines and revealed the stereochemical factors that determine the characteristic ECD data. Chirality 24:789795, 2012. (c) 2012 Wiley Periodicals, Inc.
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