Highly diastereoselective synthesis of substituted pyrrolidines using a sequence of azomethine ylide cycloaddition and nucleophilic cyclization.
Although cycloadditions of azomethine ylides usually give mixtures of endo/exo adducts, we successfully tuned the mechanistic path of a new reaction cascade to afford substituted pyrrolidines in high yields and diastereomeric purity. This was achieved by forcing the demetalation of tin- or silicon-substituted iminium ions, followed by azomethine ylide cycloaddition and nucleophilic cyclization. Structural complexity is thus built rapidly in a fully controlled one-pot reaction cascade.
Bélanger
Guillaume
G
Département de Chimie, Université de Sherbrooke, 2500 Boulevard Université, Sherbrooke, Québec J1K 2R1, Canada. guillaume.belanger@usherbrooke.ca
Darsigny
Véronique
V
Doré
Michaël
M
Lévesque
François
F
D001391:Azo Compounds / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
D001391:Azo Compounds; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine