62401-18-7

Usage

Chemical structure

A pyrrolidinone derivative with an allyl substituent and a hydroxymethyl group

Reactivity

Widely used in organic synthesis as a reagent and building block for the preparation of various compounds

Applications

Cross-linking agent in the production of polymers, resins, and adhesives
Potential applications in pharmaceutical and medicinal chemistry due to its unique chemical structure and properties

Industrial uses

Versatile compound with diverse industrial and scientific uses
Please note that some properties such as appearance, physical state, solubility, boiling point, melting point, and density are not specified in the material provided.

Upstream product

• 4931-81-1 methyl 1-allyl-5-oxopyrrolidine-2-carboxylate 
• 4931-66-2 methyl 5-oxopyrrolidine-2-carboxylate 
• 56-86-0 L-glutamic acid 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 115445-33-5 (S)-1-allyl-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester 

Downstream Products

• 1255791-51-5 01410A 
• 1255791-52-6 02110A 

Relevant academic research and scientific papers

Rhodium-Catalyzed Stereospecific C?H Amination for the Construction of Spiroaminal Cores: Reactivity Difference between Nitrenoid and Carbenoid Species against Amide Functionality

Metal nitrenoids and metal carbenoids exhibit similar reactivity for insertion into a C?H bond and a C=C double bond. These reactions have attracted the attention of organic chemists due to their unusual bond-forming ability, but the reactivity difference between these chemical species has not been studied. In this paper, we examined the reactivity difference using the corresponding Rh nitrenoid and Rh carbenoid precursors. The Rh nitrenoid inserted into an intramolecular C(sp3)?H bond adjacent to an amide nitrogen, affording functionalized spiroaminals that are ubiquitous in natural products, while the Rh carbenoid inserted into an amide C?N bond. The totally different reactivity was rationalized by the relatively low energy barrier for the C?H insertion reaction of the Rh nitrenoid. Computational analysis suggests that the origin of the discrepancy is the electrophilicity of the coordinating atoms to the Rh complex.

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