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: amino acid; aza-Michael addition; crystallization-induced diastereomer transformation; dynamic covalent chemistry; homophenylalanine; indanone; isomerization.
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