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Insights on the Pseudo-Enantiomeric Properties of Bifunctional Cinchona Alkaloid Squaramide-derived Organocatalyst

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The use of pseudo enantiomers is a well-known method of achieving products of complementary stereochemistry. Only rarely can different enantiomers of a product be accessed without modulation of the catalyst. Recently, a system was reported wherein two different enantiomers of spirocycles were obtained by a cascade reaction of unsaturated pyrrolin-4-ones with mercaptoacetaldehyde catalyzed by a single optimized cinchona alkaloid squaramide-derived organocatalyst. It was originally proposed that the E -/ Z -geometry of the unsaturated pyrrolin-4-one dictated the stereochemistry of the spirocycle product, but this was not investigated further. In the present work, we have investigated the nature of a pseudo-enantiomeric organocatalyst conformation applying density functional theory calculations for investigating the transition states for the reaction. Furthermore, the influence of the double-bond geometry of the pyrrolin-4-one has been studied beyond what is possible to test experimentally. The results provide a greater understanding for this class of reactions that may be applicable in future methodology development.

Original languageEnglish
JournalChemistry: A European Journal
Pages (from-to)15727-15732
Number of pages6
Publication statusPublished - Dec 2020

Bibliographical note

© 2020 Wiley-VCH GmbH.

    Research areas

  • Aldol reaction, Michael addition, cinchona alkaloids, density functional theory, organocatalysis

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