cis-Selective synthesis of 1,3-disubstituted tetrahydro-β-carbolines from N-sulfonyl N,S-acetals?
Organic & Biomolecular Chemistry Pub Date: 2019-10-11 DOI: 10.1039/C9OB01796H
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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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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