title: Chemoselective nucleophilic attack on N-acyl derivatives of (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG).
abstract: [reaction: see text] Heteronucleophiles and C-nucleophiles chemoselectively react with N-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of beta-hydroxy acids likely by formation and ring opening of the corresponding beta-lactones
authors.affiliation: Departamento de Química Orgánica, Universidad de Alcalá, Campus Universitario, 28871-Alcalá de Henares, Madrid, Spain.
authors.forename: Susana
authors.initials: S
authors.lastname: Mantecón
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Vaquero
authors.forename: Julio
authors.initials: J
authors.lastname: Alvarez-Builla
authors.forename: María
authors.initials: M
authors.lastname: Luz de la Puente
authors.forename: Juan F
authors.initials: JF
authors.lastname: Espinosa
authors.forename: Jesús
authors.initials: J
authors.lastname: Ezquerra
mesh_terms: D006880:Hydroxy Acids / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C484978:(S)-ethyl 4,4-dimethyl pyroglutamate; D006880:Hydroxy Acids; D007783:Lactones; D011761:Pyrrolidonecarboxylic Acid