TY - JOUR
T1 - Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide
AU - Busqué, Félix
AU - De March, Pedro
AU - Figueredo, Marta
AU - Font, Josep
AU - Gallagher, Timothy
AU - Milán, Sergio
PY - 2002/3/22
Y1 - 2002/3/22
N2 - A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable α-methoxy-N-carboxylate ion, which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate. © 2002 Elsevier Science Ltd. All rights reserved.
AB - A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable α-methoxy-N-carboxylate ion, which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate. © 2002 Elsevier Science Ltd. All rights reserved.
UR - https://www.scopus.com/pages/publications/0037155707
U2 - 10.1016/S0957-4166(02)00110-6
DO - 10.1016/S0957-4166(02)00110-6
M3 - Article
SN - 0957-4166
VL - 13
SP - 437
EP - 445
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 4
ER -