Cis-diastereoselectivity in pictet-spengler reactions of L-tryptophan and electronic circular dichroism studies

Naghmana Rashid, Samina Alam, Mashooda Hasan, Naeema Khan, Khalid M. Khan, Helmut Duddeck, Gennaro Pescitelli, Ágnes Kenéz, S. Antus, T. Kurtán

Research output: Article

12 Citations (Scopus)

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=CH3, C 2H5, C3H7, C4H 9, and C6H5) 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. 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-β-carbolines and revealed the stereochemical factors that determine the characteristic ECD data.

Original languageEnglish
Pages (from-to)789-795
Number of pages7
JournalChirality
Volume24
Issue number10
DOIs
Publication statusPublished - okt. 2012

Fingerprint

Carbolines
Dichroism
Circular Dichroism
Tryptophan
Cyclization
Aldehydes
Methylation
Carboxylic Acids
Density functional theory
Nuclear magnetic resonance
X rays
Carboxylic acids
Esters
X-Rays

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

Cis-diastereoselectivity in pictet-spengler reactions of L-tryptophan and electronic circular dichroism studies. / Rashid, Naghmana; Alam, Samina; Hasan, Mashooda; Khan, Naeema; Khan, Khalid M.; Duddeck, Helmut; Pescitelli, Gennaro; Kenéz, Ágnes; Antus, S.; Kurtán, T.

In: Chirality, Vol. 24, No. 10, 10.2012, p. 789-795.

Research output: Article

Rashid, N, Alam, S, Hasan, M, Khan, N, Khan, KM, Duddeck, H, Pescitelli, G, Kenéz, Á, Antus, S & Kurtán, T 2012, 'Cis-diastereoselectivity in pictet-spengler reactions of L-tryptophan and electronic circular dichroism studies', Chirality, vol. 24, no. 10, pp. 789-795. https://doi.org/10.1002/chir.22070
Rashid, Naghmana ; Alam, Samina ; Hasan, Mashooda ; Khan, Naeema ; Khan, Khalid M. ; Duddeck, Helmut ; Pescitelli, Gennaro ; Kenéz, Ágnes ; Antus, S. ; Kurtán, T. / Cis-diastereoselectivity in pictet-spengler reactions of L-tryptophan and electronic circular dichroism studies. In: Chirality. 2012 ; Vol. 24, No. 10. pp. 789-795.
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