596104-96-0

Upstream product

• 452096-25-2 (2S,3S,4S)-1,4-dimethyl-3-phenyl-azetidine-2-carbonitrile 
• 864360-15-6 (2S,3S,4S)-1,4-Dimethyl-3-phenyl-azetidine-2-carboxylic acid ethyl ester 

Downstream Products

• 1047987-75-6 C₁₂H₁₆FN 
• 596105-07-6 Methanesulfonic acid (2S,3S,4S)-1,4-dimethyl-3-phenyl-azetidin-2-ylmethyl ester 

Relevant academic research and scientific papers

Rearrangement of 2-hydroxyalkylazetidines into 3-fluoropyrrolidines

Upon treatment with DAST (diethylaminosulfur trifluoride) enantiopure 2-hydroxyalkylazetidines rearrange into 3-fluoropyrrolidines. The reaction is stereospecific and involves a bicyclic 1-azoniabicyclo[2.1.0]pentane intermediate which is regioselectively opened by a fluoride anion. Georg Thieme Verlag Stuttgart.

Highly stereoselective ring expansion of enantiopure α-hydroxyalkyl azetidines

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.