126908-52-9

Upstream product

• 56-86-0 L-glutamic acid 
• 4392-24-9 Cinnamyl bromide 
• 7149-65-7 ethyl (S)-pyroglutamate 

Downstream Products

• 126265-75-6 (R)-5-Methyl-1-((E)-3-phenyl-allyl)-pyrrolidin-2-one 
• 142053-17-6 1-(3-phenyl-2-propenyl)-5-hydroxymethyl-2-pyrrolidinone methanesulfonate 
• 126265-64-3 1-(3-phenyl-2-propenyl)-5-iodomethyl-2-pyrrolidinone 
• 126265-70-1 6-benzyl-tetrahydropyrrolizin-3-one 
• 126908-56-3 1-(3-phenyl-2-propenyl)-5-hydroxymethyl-2-pyrrolidinone 

Relevant academic research and scientific papers

Asymmetric radical cyclizations: The synthesis of 6-alkyl pyrrolizidin-2-ones

This work describes the use of ethyl (5S)-carboethoxy-2-pyrrolidinone (ethyl pyroglutamate) as a chiral starting material for use in radical cyclization reactions. Pyroglutamate is converted to a 5-iodomethyl-N-allylic-2-pyrrolidinone that undergoes radical cyclization under mild conditions. The products are 6-substituted pyrrolizidinone derivatives, produced with high diastereoselectivity.

AN IMPROVED REDUCTION OF THE ESTER MOIETY IN N-SUBSTITUTED PYROGLUTAMATES

Lithium borohydride reduction of N-functionalized pyroglutamates failed to give the corresponding hydroxymethyl derivative.Reduction with lithium aluminium hydride bound to dry silica gel, however, gace excellent yields of chiral 5-hydroxymethyl-1-allyl-2

ASYMMETRIC SYNTHESIS OF PYRROLIZIDINONES BY RADICAL CYCLIZATION OF N-ALLYLIC PYROGLUTAMATES

Ethyl S-pyroglutamate is converted to N-allylic-S C5-iodomethyl-2-pyrrolidinone.Facile radical cyclization on treatment with AIBN and tributyltin hydride in refluxing benzene gives good yields of the C6 substituted pyrrolizidin-2-one