TY - JOUR
T1 - From pyrrolidin-2-ones to 3-aza-2-oxobicyclo[3.2.0]heptanes. Synthesis of both enantiomers of cis-2-aminomethylcyclobutane carboxylic acid, a conformationally restricted analogue of GABA
AU - Galeazzi, Roberta
AU - Mobbili, Giovanna
AU - Orena, Mario
PY - 1999/1/1
Y1 - 1999/1/1
N2 - By changing the cyclisation conditions (NaH in THF or NaOEt in EtOH), an enantiopure malonamide containing an enoate acceptor afforded either diastereomeric pyrrolidin-2-one 3 or 4 as the major product of the intramolecular conjugate addition. After separation, both diastereomers were converted through simple steps into the corresponding 3-aza-2- oxobicyclo[3.2.0] heptane which eventually led to each enantiomer of cis-2- aminomethylcyclobutanecarboxylic acid, 1, a conformationally restricted analogue of GABA, in both enantiomerically pure form.
AB - By changing the cyclisation conditions (NaH in THF or NaOEt in EtOH), an enantiopure malonamide containing an enoate acceptor afforded either diastereomeric pyrrolidin-2-one 3 or 4 as the major product of the intramolecular conjugate addition. After separation, both diastereomers were converted through simple steps into the corresponding 3-aza-2- oxobicyclo[3.2.0] heptane which eventually led to each enantiomer of cis-2- aminomethylcyclobutanecarboxylic acid, 1, a conformationally restricted analogue of GABA, in both enantiomerically pure form.
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U2 - 10.1016/S0040-4020(98)01031-X
DO - 10.1016/S0040-4020(98)01031-X
M3 - Article
AN - SCOPUS:0032927046
VL - 55
SP - 261
EP - 270
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 1
ER -