596104-98-2Relevant academic research and scientific papers
Highly stereoselective ring expansion of enantiopure α-hydroxyalkyl azetidines
Couty, Fran?ois,Durrat, Fran?ois,Prim, Damien
, p. 5209 - 5212 (2007/10/03)
Stereodefined α-hydroxyalkyl azetidines, prepared in a few steps from enantiopure β-amino alcohols, are chlorinated or transformed into methanesulfonyloxymethyl derivatives in good yields. Heating of these compounds in chloroform or dimethylformamide induces a stereospecific ring enlargement to give 3-chloro or 3-methanesulfonyloxy pyrrolidines. The ease of this rearrangement depends on the nature of the migrating group (Cl- or MsO-), of the class of the starting alcohol (primary or secondary) and of the relative stereochemistry of the starting material.
