SN2 vs. E2 on quaternary centres: an application to the synthesis of enantiopure beta2,2-amino acids.
S(N)2 and E2 competing reactions in cyclic sulfamidates can be modulated by the change of an amide group to an ester group attached to the quaternary carbon activated for the nucleophilic attack, allowing an easy approach to enantiopure alpha,alpha-disubstituted beta-amino acids.
Avenoza
Alberto
A
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., E-26006 Logroño, Spain. alberto.avenoza@dq.unirioja.es
Busto
Jesús H
JH
Corzana
Francisco
F
Jiménez-Osés
Gonzalo
G
Peregrina
Jesús M
JM
D000596:Amino Acids / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry
D000596:Amino Acids; D004952:Esters; D013449:Sulfonamides; D005459:Fluorides