114677-02-0Relevant academic research and scientific papers
Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives
Heindl, Cornelia,Huebner, Harald,Gmeiner, Peter
, p. 3141 - 3152 (2007/10/03)
Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2long, D2short, D3 and D4 as well as 5-HT1A and 5-HT2, respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21, the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed.
Electrophilic Olefin Heterocyclization in Organic Synthesis. Highly Stereoselective Synthesis of Trans 3,5-Disubstituted Pyrrolidin-2-ones by Iodolactamization via Homoallylic Asymmetric Induction
Takahata, Hiroki,Takamatsu, Tamotsu,Chen, Yin-Shan,Ohkubo, Naoki,Yamazaki, Takao,et al.
, p. 3792 - 3797 (2007/10/02)
α-Substituted γ,δ-unsaturated thioimidates 19-24, prepared by methylation of the corresponding thioamides 13-18, undergo iodine-induced lactamization to provide the 3,5-disubstituted pyrrolidin-2-ones 25a,b-30a,b.High 1,3-asymmetric induction by the homoa
