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Stereochemical switch driven by crystallization: Interplay between stoichiometry and configuration of the products.

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An intriguing example of a crystallization-induced stereochemical switch in the configuration of aza-Michael reaction products is described. Depending on both the stereochemical purity and stoichiometric ratio of the chiral amine… Click to show full abstract

An intriguing example of a crystallization-induced stereochemical switch in the configuration of aza-Michael reaction products is described. Depending on both the stereochemical purity and stoichiometric ratio of the chiral amine used, the reaction delivers crystalline diastereomers of a different stereochemistry. The optically pure diastereomer smoothly converts to its racemic epimer salt upon the addition of a complementary chiral amine.

Keywords: switch driven; stereochemical switch; crystallization; configuration; driven crystallization

Journal Title: Chirality
Year Published: 2022

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