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.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c9ob01796h | DOI Listing |
Publication Analysis
Top Keywords
cis-selective synthesis
4
synthesis 13-disubstituted
4
13-disubstituted tetrahydro-β-carbolines
4
tetrahydro-β-carbolines n-sulfonyl
4
n-sulfonyl ns-acetals
4
ns-acetals nucleophilic
4
nucleophilic addition
4
addition grignard
4
grignard reagents
4
reagents tetrahydro-β-carboline
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!