492435-16-2

Upstream product

• 82270-62-0 (S)-N-benzylmandelamide 
• 79-31-2 isobutyric Acid 
• 79-30-1 isobutyryl chloride 
• 17199-29-0 (S)-Mandelic acid 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones from chiral O-acylmandelamides or lactamides

(-)-O-Acyllactamides or mandelamides in the presence of TBSOTf underwent cyclization reaction to give optically active 2-oxy-1,3-oxazolidin-4-ones, a novel nitrogen analog of orthoesters, in good yields. An X-ray analysis and NOE studies indicated that the absolute configuration at the newly formed chiral carbon was S. For their synthetic application, the 1,3-dipolar cycloaddition of nitrile oxide was examined. The cycloadducts were obtained in a stereoselective manner. Subsequent treatment of the adduct with TBAF resulted in the one-step removal of mandelamide, giving optically active 4,5-dihydroisoxazole and mandelamide in good yields.

Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones and an efficient synthesis of optically active secondary 2-pyrrolidones

Treatment of (-)-O-acyllactamides or mandelamides with TBSOTf in the presence of base gives optically active 2-oxy-1,3-oxazolidin-4-ones stereoselectively, which serve as useful precursors for the preparation of optically active secondary 2-pyrrolidones via radical cyclization and subsequent one-step removal of mandelic acid.