Premium
Stereoselective Mannich Reaction Driven by Crystallization
Author(s) -
Čierna Michaela,
Markus Jozef,
Doháňošová Jana,
Moncol Ján,
Jakubec Pavol,
Berkeš Dušan,
Caletková Oľga
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000774
Subject(s) - chemistry , diastereomer , stereoselectivity , mannich reaction , crystallization , epimer , reagent , combinatorial chemistry , stoichiometry , enantiomer , organic chemistry , catalysis
Herein we disclose an efficient and experimentally straightforward method for the stereoselective synthesis of a variety of α‐substituted Mannich salts. This direct three‐component Mannich reaction operates on readily available reagents in almost stoichiometric ratio and enables the preparation of both enantiomers. Crystallization controlled epimerization allows isolation of the target compounds in high enantio‐ and diastereomeric purities by a simple filtration. The efficiency of this chromatography‐free approach predestines it for the gram‐scale synthesis and industrial applications.