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

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 s...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2022-07, Vol.34 (7), p.948-954
Main Authors: Čierna, Michaela, Berkeš, Dušan, Baran, Peter, Šoral, Michal, Kolarovič, Andrej, Jakubec, Pavol
Format: Article
Language:English
Subjects:
amino acid
aza‐Michael addition
Configurations
Crystallization
crystallization‐induced diastereomer transformation
Diastereoisomers
dynamic covalent chemistry
homophenylalanine
indanone
isomerization
Michael reaction
Reaction products
Stereochemistry
Stoichiometry
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Summary: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.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23451