492435-13-9

Upstream product

• 17199-29-0 (S)-Mandelic acid 
• 107-11-9 1-amino-2-propene 
• 13704-09-1 (S)-(-)-ethyl mandelate 
• 492435-19-5 (S)-(+)-O-bromoacetyl-N-allylmandelamide 

Downstream Products

• 492435-20-8 (S)-(+)-O-(phenylseleno)acetyl-N-allylmandelamide 
• 492435-17-3 (S)-(+)-O-acetyl-N-allylmandelamide 
• 492435-19-5 (S)-(+)-O-bromoacetyl-N-allylmandelamide 
• 604783-91-7 (S)-(+)-O-(2-iodo)benzoyl-N-allylmandelamide 
• 492435-12-8 (2S,6R,7aS)-7a-(tert-butyldimethylsilyl)oxy-6-methyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one 
• 492435-28-6 (2S,5S)-N-allyl-2-(tert-butyldimethylsilyl)oxy-5-phenyl-2-(phenylseleno)acetyl-1,3-oxazolidin-4-one 
• 604783-96-2 (5S)-N-allyl-2-(tert-butyldimethylsilyl)oxy-2-(2-iodophenyl)-5-phenyl-1,3-oxazolidin-4-one 
• 492435-27-5 (2S,5S)-N-allyl-2-(tert-butyldimethylsilyl)oxy-2-bromomethyl-5-phenyl-1,3-oxazolidin-4-one 

Relevant academic research and scientific papers

Biocatalytic aminolysis of ethyl (S)-mandelate by lipase from Candida antarctica

Enzymes play many roles in the advancement of biotechnology, discovery of new therapeutic agents and industrial processes. In this perspective, aminolysis reactions using lipase from Candida antarctica (CAL-B) were performed from ethyl (S)-mandelate and several aliphatic amines (45 °C, hexane, 3–6 h). By means of optimized conditions, amides with excellent isolated yields (60–97%) were synthetized. The biotechnological potential of CAL-B as a promising approach for the synthesis of organic compounds in a more sustainable, rapid, efficient and green chemistry perspective was verified on these results.

Oxyoxazolidinone as an auxiliary for heterocyclic synthesis. Enantioselective formation of N-unprotected 2-pyrrolidones from selenocarboxylate and allylamines via radical cyclization

Optically active N-unprotected 2-pyrrolidones were prepared in a highly stereoselective manner through radical cyclization reaction of oxyoxazolidinone. Asymmetric induction from the oxyoxazolidinone ring system was generally high and oxazabicyclo[3.3.0]octanones were obtained in good yields. Treatment of the bicyclic compounds with TBAF resulted in the one-step cleavage of C-O and C-N bond, directly giving secondary 2-pyrrolidones in good yields along with recovery of chiral mandelic acid without loss of optical purity. The use of the present procedure gave optically active 4,5-disubstituted N-unprotected 2-pyrrolidone derivatives trans selectively.

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.