Stereoselective Mannich Reaction Driven by Crystallization. Issue 35 (9th September 2020)

• Record Type: Journal Article
• Authors: Čierna, Michaela; Markus, Jozef; Doháňošová, Jana; Moncol, Ján; Jakubec, Pavol; Berkeš, Dušan; Caletková, Oľga
• Is Part Of: European journal of organic chemistry. Issue 35(2020)
• Page Start: 5685
• Page End: 5689
• Publication Date: 2020-09-09
• Subjects: Asymmetric synthesis -- Crystallization -- Diastereoselectivity -- Mannich bases -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000774
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : An efficient direct three‐component Mannich reaction for the stereoselective synthesis of a variety of aromatic β‐amino ketones is described. Crystallization‐controlled epimerization enables the isolation of the target compounds in high enantio‐ and diastereomeric purities by a simple filtration.