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• W2395348535 abstract "The diastereoselective synthesis of optically active 1,3-disubstituted tetrahydro-β-carbolines using polar protic Pictet-Spengler cyclization of (S)-tryptophan methyl ester with five aldehydes RCHO (R═CH(3), C(2)H(5), C(3)H(7), C(4)H(9), and C(6)H(5)) was studied. As an alternate route, the cyclization of (S)-tryptophan with the same aldehydes and subsequent methylation of the resulting tetrahydro-β-carboline carboxylic acids were also performed for comparison. (13)C 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-β-carbolines and revealed the stereochemical factors that determine the characteristic ECD data." @default.
• W2395348535 created "2016-06-24" @default.
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• W2395348535 date "2012-07-04" @default.
• W2395348535 modified "2023-09-26" @default.
• W2395348535 title "<i>Cis</i>-Diastereoselectivity in Pictet-Spengler Reactions of<scp>L</scp>-Tryptophan and Electronic Circular Dichroism Studies" @default.
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• W2395348535 doi "https://doi.org/10.1002/chir.22070" @default.
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