224561-57-3

Upstream product

• 129823-21-8 3-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 78027-57-3 (RS)-N-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 100-46-9 benzylamine 

Downstream Products

• 328047-13-8 Acetic acid 3-acetoxy-1-benzyl-5-oxo-pyrrolidin-2-yl ester 
• 130781-14-5 Acetic acid (2R,3S)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester 
• 130781-14-5 Acetic acid (2R,3R)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester 
• 141837-20-9 4-tosyl-N-benzylpyrrolidin-2-one 
• 125370-52-7 (±)-1-benzyl-4-hydroxypyrrolidin-2-one 

Relevant academic research and scientific papers

Photolysis of olefinic N-chloropyrrolidinones, N-chlorosuccinimides and N-chloro-oxazolidinones: Reactivity of cyclic carboxamidyl, imidyl and carbamyl radicals in intramolecular reactions

N-Chloro-alkenylpyrrolidinones, an N-chloro-alkenylsuccinimide and N- chloro-alkenyloxazolidinones were prepared as precursors of olefinic cyclic carboxamidyl, imidyl and carbamyl radicals constrained to undergo intramolecular reactions uniquely via their planar or slightly twisted (30- 35°) Π(N) state (1,5-transfer of an allylic hydrogen, 5-exo or 6-exo cyclization to give bicyclo[2.2.1]azaheptane and bicyclo[3.2.1]azaoctane skeletons respectively), those intramolecular reactions being unaccessible to the planar ΣN state. Their photolysis gave products arising uniquely from intermolecular reactions of those nitrogen radicals (addition to an external olefin, hydrogen abstraction from the solvent, allylic hydrogen abstraction). An intramolecular reaction leading to bicyclo[3.3.0]azaoctane derivatives via 5-exo cyclization was observed with an N-chloro-alkenylpyrrolidinone and an N-chloro-alkenyloxazolidinone. In these two cases, both the Π(N) and the Σ(N) states of the cyclic amidyl radical allow orbital overlap for 5-exo cyclization.

Stereoselective synthesis of statin analogues

Statin analogues can be synthesized stereoselectively (diastereomeric ratios up to 4:1) starting from malic acid. The key step involves an unprecedented cis-selective allylation of an α-alkoxy N-acyliminium ion.