Tuning the sense of product stereochemistry in aldol reactions of acetone and aromatic aldehydes in the presence of water with a single chiral catalyst

Autor:	Mihály Bartók, András A. Gurka, Gabor London, György Szőllősi, Kornél Szőri
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Enantioselective synthesis Salt (chemistry) Biochemistry Catalysis chemistry.chemical_compound chemistry Aldol reaction Drug Discovery Emulsion Acetone Organic chemistry
Zdroj:	Tetrahedron Letters. 56:7201-7205
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2015.11.051
Popis:	We report the aldol addition of acetone to aromatic aldehydes in the presence of a large amount of water where the stereochemical outcome of the reactions can be tuned with achiral salt additives using a single proline-derived catalyst. Depending on the nature of the added salt the ( R ) and ( S ) enriched products could be obtained. In the reaction of 2-nitrobenzaldehyde with acetone, NaOAc promoted the formation of the ( S )-enantiomer (20% ee) while using NH 4 Cl the ( R )-enantiomer was obtained in excess (58% ee). A similar inversion was observed for several other aromatic aldehydes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f6618434a55400a027266d9119c76bc8 https://doi.org/10.1016/j.tetlet.2015.11.051 Zobrazit plný text záznamu Full Text from ScienceDirect