A general synthesis of 2-alkoxy-2-phenylpropanoic acids

Autor:	Keith A. Monk, Nathan C. Duncan, Charles M. Garner, Eric A. Bauch
Rok vydání:	2008
Předmět:	chemistry.chemical_compound Chemistry Yield (chemistry) Organic Chemistry Drug Discovery Diastereomer Alkoxy group Organic chemistry Methanol Primary alcohol Enantiomer Ring (chemistry) Biochemistry
Zdroj:	Tetrahedron. 64:8605-8609
ISSN:	0040-4020
Popis:	A preparation of a variety of 2-alkoxy-2-phenylpropanoic acids in two steps is described. Epoxidation of α-methylstyrene with mCPBA in methanol or primary alcohol solvents proceeded with an acid-catalyzed in situ ring opening reaction to give the corresponding 2-alkoxy-2-phenyl-1-propanols in 28–91% yield. Lower yields were realized with secondary (22–58%) and tertiary (14%) alcohols. These alcohols were cleanly oxidized to the corresponding carboxylic acids using a mild Heyns' oxidation (O2, Pt/C) in generally good to excellent yields (25–92%). The derived (S)-α-methylbenzylamide diastereomers are nearly all well separated by capillary GC, and the use of this method to determine the enantiomeric purity of brucine-resolved 2-methoxy-2-phenylpropanoic acid was demonstrated.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::338ef063545df18ebac8c29c98962f3d https://doi.org/10.1016/j.tet.2008.06.105 Zobrazit plný text záznamu Full Text from ScienceDirect