27948-40-9Relevant articles and documents
Separation of (S)-(-)-3-methyl-2-pyrrolidinone as an inclusion complex with (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis(hydroxydiphenylmethyl) -1,1′-biphenyl host and its X-ray structural study
Le Roex, Tanya,Nassimbeni, Luigi R.,Toda, Fumio
, p. 77 - 79 (2008/09/19)
By inclusion complexation with the chiral host compound (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis(hydroxydiphenylmethyl) -1,1′-biphenyl, racemic 3-methyl-2-pyrrolidinone was resolved and its (S)-(-)-enantiomer was isolated as a 1:1 inclusion complex, which crystallises in the orthorhombic crystal system in the space group P212 121 (a = 14.1163(2) A, b = 14.7140(3) A, c = 17.2025(3) A). By the inclusion complexation, the keto-enol equilibrium of the guest was frozen and the keto-form was isolated in a pure form. By X-ray structural study of the complex, the guest molecule included was elucidated to be the keto-form and its absolute configuration was determined to be (S).
Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam
Baussanne, Isabelle,Travers, Catherine,Royer, Jacques
, p. 797 - 804 (2007/10/03)
3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by α-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce γ-aminobutyric acid (GABA) analogue 13.
