569682-65-1

Upstream product

• 501-53-1 benzyl chloroformate 
• 569682-63-9 (-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester 
• 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 
• 569682-60-6 benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en-1-yl)carbamate 
• 569682-62-8 N-(2,2-dimethoxyethyl)-N-(2-oxoethyl) carbamic acid benzyl ester 
• 114790-39-5 benzyl N-(2,2-dimethoxyethyl)carbamate 

Downstream Products

• 569682-61-7 (3R,4R)-4-aminopyrrolidine-3-carboxylic acid 

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.