604783-96-2

Upstream product

• 492435-27-5 (2S,5S)-N-allyl-2-(tert-butyldimethylsilyl)oxy-2-bromomethyl-5-phenyl-1,3-oxazolidin-4-one 
• 492435-13-9 (S)-N-allyl-2-hydroxy-2-phenylacetamide 
• 17199-29-0 (S)-Mandelic acid 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 604783-91-7 (S)-(+)-O-(2-iodo)benzoyl-N-allylmandelamide 

Relevant academic research and scientific papers

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.