Issue 43, 2019

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.

Graphical abstract: cis-Selective synthesis of 1,3-disubstituted tetrahydro-β-carbolines from N-sulfonyl N,S-acetals

Supplementary files

Article information

Article type
Paper
Submitted
14 Aug 2019
Accepted
09 Oct 2019
First published
11 Oct 2019

Org. Biomol. Chem., 2019,17, 9510-9513

cis-Selective synthesis of 1,3-disubstituted tetrahydro-β-carbolines from N-sulfonyl N,S-acetals

S. Luo, Y. Liu, M. J. Lambrecht, D. F. Ortwine, A. G. DiPasquale, J. Liang, X. Wang, J. R. Zbieg and J. Li, Org. Biomol. Chem., 2019, 17, 9510 DOI: 10.1039/C9OB01796H

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