Unraveling the Role of Supramolecular Additives in a Proline‐Catalyzed Reaction. Issue 1 (6th December 2018)

• Record Type: Journal Article
• Authors: Martín, Judith; Merino, Isabel; Fanjul‐Mosteirín, Noé; Mendoza‐Meroño, Rafael; García‐Granda, Santiago; Concellón, Carmen; del Amo, Vicente
• Is Part Of: European journal of organic chemistry. Issue 1(2019)
• Page Start: 188
• Page End: 198
• Publication Date: 2018-12-06
• Subjects: Hydrogen bonds -- NMR spectroscopy -- Organocatalysis -- Proline -- Supramolecular chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801509
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Various additives, typically based on molecules featuring H‐bond donor motifs, have been essayed towards improving the catalytic properties of proline. However, their mode of action is not clear yet. By employing in situ 1 H and 19 F NMR DOSY experiments, the role of a tetrafluoroborate guanidinium salt in a novel proline‐catalyzed cross‐aldol reaction between α, α‐dichloroacetone and aromatic aldehydes has been fully disclosed. Abstract : The cooperative participation of a TBD‐derived guanidinium salt and proline promotes the cross‐aldol reaction between α, α‐dichloroacetone and aromatic aldehydes. NMR DOSY experiments allow disclosing the mode of action of this additive, which operated through H‐bonding interactions.