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cis-Selective Synthesis of 1,3-Disubstituted Tetrahydro-β-Carbolines from N-Sulfonyl N,S-Acetals

Abstract

Nucleophilic addition of Grignard reagents to tetrahydro-β-carboline (THC) N-sulfonyl N,S-acetal generates exclusively cis-1,3-disubstituted THCs with a unique 1,3-diaxial conformation. The stereochemical relationship of the 1,3-substituents was confirmed by 2-dimensional NMR spectroscopy and X-ray crystallography. The mechanism of the reaction is proposed based on crystal structures and molecular orbital calculations.

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Publication details

The article was received on 14 Aug 2019, accepted on 09 Oct 2019 and first published on 11 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB01796H
Org. Biomol. Chem., 2019, Accepted Manuscript

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    cis-Selective Synthesis of 1,3-Disubstituted Tetrahydro-β-Carbolines from N-Sulfonyl N,S-Acetals

    J. R. Zbieg, J. Li, X. Wang, J. Liang, D. F. Ortwine, A. DiPasquale, Y. Liu, L. S. Luo and M. J. Lambrecht, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB01796H

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