210415-84-2

Upstream product

• 210415-78-4 (R)-4-(Benzyl-hydroxy-amino)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-ynoic acid methyl ester 
• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 
• 210415-80-8 (Z)-(R)-4-(Benzyl-hydroxy-amino)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester 

Downstream Products

• 210415-87-5 (5R)-1-benzyl-5-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-pyrrolidinone 

Relevant academic research and scientific papers

Ready access to enantiopure 5-substituted-3-pyrrolin-2-ones from N- benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN)

The reaction of the lithiated salt of methyl propiolate with N-benzyl- 2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) afforded the corresponding propargyl hydroxylamines in a stereocontrolled way depending on the nature of the Lewis acid used as an additive. Subsequent reduction of the obtained hydroxylamines provided chiral 5-substituted-3-pyrrolin-2-ones, in high overall yields.