𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones

✍ Scribed by Emanuela Crucianelli; Roberta Galeazzi; Gianluca Martelli; Mario Orena; Samuele Rinaldi; Piera Sabatino

Book ID
108283144
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
371 KB
Volume
66
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

πŸ“œ SIMILAR VOLUMES

Synthesis of a conformationally restrict
Synthesis of a conformationally restricted analog of pregabalin by stereoselective alkylation of a chiral pyrrolidin-2-one
✍ Roberta Galeazzi; Gianluca Martelli; Giovanna Mobbili; Mario Orena; Samuele Rina πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 English βš– 140 KB

The 4-benzyloxymethyl pyrrolidin-2-one, 5, was alkylated leading to 3,4-trans-disubstituted pyrrolidin-2-one 6 in good yield and total diastereoselection, as shown by 1 H NMR data and NOE experiments. After reduction of the carbonyl group to give the trans-3,4-disubstituted pyrrolidine 7, and remova

From pyrrolidin-2-ones to 3-aza-2-oxobic
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
✍ Roberta Galeazzi; Giovanna Mobbili; Mario Orena πŸ“‚ Article πŸ“… 1999 πŸ› Elsevier Science 🌐 French βš– 563 KB

By changing the cyclisation conditions (Nail 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 thr