A. Nuhrich, J. Moulines
May 6, 1991
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron
Abstract
Abstract The cyclisation of N -tosyl-oxiranepropylamines is accomplished in aqueous basic medium and in anhydrous acid medium as well. In most cases, this reaction occurs by a regiospecific 5- exo-tet . ring closure and affords N -tosyl-2-pyrrolidinemethanols in high yields. The formation of N -tosyl-3-piperidinols through endo attack on the epoxide linkage is observed only in systems exhibiting geometric constraints in the transition state. These cyclisations are accompanied by inversion of configuration at the carbon undergoing nucleophilic attack. Thus, the N -tosyl-oxiranepropylamines cyclisation opens up an efficient entry to functional pyrrolidines and is expected to find useful applications in synthesis.