54712-22-0

Upstream product

• 299-42-3 ephedrine 
• 770-12-7 O-phenyl phosphorodichloridate 
• 50-98-6 ephedrine hydrochloride 
• 54750-13-9 (2S,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one 
• 139-02-6 sodium phenoxide 

Relevant academic research and scientific papers

Totally stereoselective P-O to P-C migration rearrangement: Application to the synthesis of new chiral O-hydroxyaryl phosphine oxides

The synthesis of a novel class of chiral o-hydroxyaryl phosphine oxides by the rearrangement of a P-O to a P-C bond is described. This reaction proceeds with excellent yields (75-95%) and total retention of the configuration on the phosphorus atom. In the case of the treatment of an equimolar mixture of the diastereomers anti-2e and syn-2f, the resulting compounds anti-3e and syn-3f, obtained in a 1:1 molar ratio, were separated and characterized by X-ray diffraction. On the basis of the experimental results, we suggest that the migration mechanism is addition-pseudorotation-elimination; this explains the total stereoselectivity observed at the phosphorus atom.