TY - JOUR
T1 - Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid
AU - Galeazzi, Roberta
AU - Geremia, Silvano
AU - Mobbili, Giovanna
AU - Orena, Mario
PY - 1996
Y1 - 1996
N2 - By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from 1H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.
AB - By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from 1H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.
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U2 - 10.1016/0957-4166(95)00423-8
DO - 10.1016/0957-4166(95)00423-8
M3 - Article
AN - SCOPUS:0030051942
VL - 7
SP - 79
EP - 88
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 1
ER -