756845-36-0

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 117811-87-7 (2S,4R)-4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 

Downstream Products

• 756845-39-3 (-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one 
• 756845-41-7 (+)-(3S,4R,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one 

Relevant academic research and scientific papers

Novel asymmetric approach to proline-derived spiro-β-lactams

We describe a novel asymmetric approach using Staudinger chemistry to proline-derived spiro-β-lactams. A chiral group at C-4 of the acid chloride of proline directs the stereoselectivity of Staudinger chemistry and later is sacrificed to obtain optically active 5.4-spiro-β-lactams. The scope, limitations, and mechanistic rationale for the observed results of Staudinger Chemistry of the acid chloride of 4-alkyl(aryl)sulfonyloxy-L-proline with imines are also discussed.