Diastereoselective synthesis of N-secondary alkyl 2-alkoxymethylpyrrolidines via sequential addition reactions of organolithium and -magnesium reagents to N-thioformyl 2-alkoxymethylpyrrolidines.
Highly efficient sequential addition reactions of organolithium and -magnesium reagents to N-thioformyl 2-methoxymethylpyrrolidine have been described. Various combinations of these reagents gives successful results. A highly efficient and diastereoselective addition reaction is also described. Use of the opposite combinations of substituents on organolithium and -magnesium reagents leads to the selective formation of the opposite diastereomers. The reaction was extended to N-thioformyl 2-siloxymethypyrrolidine and 2-methoxymethylpiperidine, and these showed similar efficiency and selectivity.
Murai
Toshiaki
T
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan. mtoshi@gifu-u.ac.jp
Asai
Fumio
F
D001965:Bromides / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D015195:Drug Design; D005559:Formamides / Q000737:chemistry; D008024:Ligands; D008094:Lithium / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry; D008956:Models, Chemical; D011759:Pyrrolidines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D001965:Bromides; D005559:Formamides; D008024:Ligands; D011759:Pyrrolidines; D012997:Solvents; D008094:Lithium; D008274:Magnesium