569682-63-9

Upstream product

• 569682-60-6 benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en-1-yl)carbamate 
• 114790-39-5 benzyl N-(2,2-dimethoxyethyl)carbamate 
• 214899-24-8 (+)-diethyl [(1R,3R)-1,3-dioxo-1,3-dithian-2-yl]phosphonate 
• 569682-62-8 N-(2,2-dimethoxyethyl)-N-(2-oxoethyl) carbamic acid benzyl ester 

Downstream Products

• 569682-65-1 (+)-cis-(4S,3R)-4-benzylaminopyrrolidine-1,3-dicarboxylic acid-1-benzyl ester 
• 569682-61-7 (3R,4R)-4-aminopyrrolidine-3-carboxylic acid 
• 569682-64-0 (+)-[1'R,3'R]-1-benzyl-1',3'-dioxospiro[1',3'-dithiane-2',3-pyrrolo[3,4-c]isoxazole]-5-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid.

Intramolecular 1,3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5,5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic, (-)-cispentacin. An asymmetric synthesis of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out using the intramolecular nitrone cycloaddition as the stereocontrolling step.