Chemoselective nucleophilic attack on N-acyl derivatives of (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG).
[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
Mantecón
Susana
S
Departamento de Química Orgánica, Universidad de Alcalá, Campus Universitario, 28871-Alcalá de Henares, Madrid, Spain.
Vaquero
Juan J
JJ
Alvarez-Builla
Julio
J
Luz de la Puente
María
M
Espinosa
Juan F
JF
Ezquerra
Jesús
J
D006880:Hydroxy Acids / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism
C484978:(S)-ethyl 4,4-dimethyl pyroglutamate; D006880:Hydroxy Acids; D007783:Lactones; D011761:Pyrrolidonecarboxylic Acid