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Updated: Jun 28, 2026

Applications of Liquid-Chromatography Tandem Mass Spectrometry in Natural Products Research: Tropane Alkaloids as a Case Study
Published on: March 8, 2024
Estimating the stereoinductive potential of cinchona alkaloids with a prochiral probe approach
Yin Wei1, G Narahari Sastry, Hendrik Zipse
1Department of Chemistry and Biochemistry, LMU München, Butenandtstrasse 5-13, D-81377 München, Germany.
Abstract:
Cinchona alkaloids occupy a privileged status due to their optimal possession of two desirable properties, namely catalytic efficiency and stereoselectivity. This paper proposes a new quantitative measure, the energy difference between the adducts formed by re and si face attack to Mosher's cation (DeltaMOSCA(re-si)) as a measure of stereoinductive potential, by taking the example of cinchona alkaloids. Other descriptors such as methyl cation affinities and the one based on continuous symmetry measures are also estimated and correlated with DeltaMOSCA(re-si) values.
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