TY - JOUR
T1 - Stereoselective reactions of lithium enolates derived from N-BOC protected pyroglutamic esters
AU - Ezquerra, Jesús
AU - Pedregal, Concepción
AU - Rubio, Almudena
AU - Yruretagoyena, Belén
AU - Escribano, Ana
AU - Sánchez-Ferrando, Francisco
PY - 1993/9/17
Y1 - 1993/9/17
N2 - The lithium enolates of N-Boc protected pyroglutamic ethyl or tert-butyl esters react with electrophiles in good yield without epimerization of the chiral centre. With benzyl bromides the process is stereospecific, yielding exclusively the trans isomer. However, with other reactive electrophiles a 2:1 trans/cis diastereomeric mixture was obtained, regardless of the steric bulk of the ester group. © 1993.
AB - The lithium enolates of N-Boc protected pyroglutamic ethyl or tert-butyl esters react with electrophiles in good yield without epimerization of the chiral centre. With benzyl bromides the process is stereospecific, yielding exclusively the trans isomer. However, with other reactive electrophiles a 2:1 trans/cis diastereomeric mixture was obtained, regardless of the steric bulk of the ester group. © 1993.
U2 - 10.1016/S0040-4020(01)96272-6
DO - 10.1016/S0040-4020(01)96272-6
M3 - Article
SN - 0040-4020
VL - 49
SP - 8665
EP - 8678
JO - Tetrahedron
JF - Tetrahedron
IS - 38
ER -