881733-92-2Relevant academic research and scientific papers
A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine
Rodríguez, Dídac,Picó, Anna,Moyano, Albert
scheme or table, p. 6866 - 6869 (2009/04/07)
The first enantio- and diastereoselective approach to both 2-(2′-oxiranyl)piperidines and to 2-(2′-oxiranyl)pyrrolidines is reported. The method relies on the Sharpless asymmetric epoxidation of allyl alcohols as the sole source of chirality, and involves as the key step the base-mediated cyclization of (α-aminoalkyl)oxiranes functionalized at the ε{lunate} (or δ) position. The asymmetric synthesis of (+)-α-conhydrine illustrates the applicability of this strategy to the preparation of biologically active 2-(1-hydroxyalkyl)piperidine alkaloids.
Highly chiral muscarinic ligands: The discovery of (2S,2′R,3′S, 5′R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxide methyl iodide, a potent, functionally selective, M2 partial agonist
Scapecchi, Serena,Matucci, Rosanna,Bellucci, Cristina,Buccioni, Michela,Dei, Silvia,Guandalini, Luca,Martelli, Cecilia,Manetti, Dina,Martini, Elisabetta,Marucci, Gabriella,Nesi, Marta,Romanelli, Maria Novella,Teodori, Elisabetta,Gualtieri, Fulvio
, p. 1925 - 1931 (2007/10/03)
By further steric complication of previously studied highly chiral muscarinic agonists, we have obtained a small chiral library of enantiomeric and diasteromeric 1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxides. Binding studies on cloned
