214334-48-2

Upstream product

• 214334-42-6 (2S,5S)-2-Allyl-5-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 214334-46-0 (2R,5S)-2-Heptyl-5-(3-hydroxy-propyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 214334-45-9 (2S,5R)-2-Allyl-5-heptyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 214334-41-5 (2S,5S)-2-Allyl-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 214334-40-4 (2S,5S)-5-allyl-2-hydroxymethylpyrrolidine 
• 188015-40-9 (5S,7aS)-5-Allyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 
• 188015-47-6 (S)-2-Hydroxy-5-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 188015-58-9 (5R,7aS)-5-Ethoxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 
• 501-53-1 benzyl chloroformate 
• 135697-21-1 (S)-(1-tert-butoxycarbonyl-5-oxopyrrolidin-2-yl)-methyl-4-methylbenzenesulfonate 
• 676-58-4 methylmagnesium chloride 
• 214334-47-1 (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester 

Downstream Products

• 159425-05-5 (2R,5S)-2-Heptyl-5-(3-oxo-butyl)-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Highly stereoselective trans addition of π-type nucleophiles to a bicyclic N-acyliminium ion - Application to the synthesis of indolizidine and pyrrolizidine alkaloids

Enantiopure bicyclic 5-ethoxytetrahydropyrrolo[1,2-c]oxazol-3-one 1b was prepared in two steps from the known tosylate 4, which is readily available from (S)-pyroglutamic acid. Trapping of the N-acyliminium ion (I), generated in situ from 1b in the presence of Lewis acid, with various silylated π-type nucleophiles gave rise selectively to trans adducts 2. The usefulness of this stereoselective access to trans-2,5-disubstituted pyrrolidines was illustrated by formal syntheses of 3,5-disubstituted indolizidine toxins, starting from 5-allyltetrahydropyrrolo[1,2-c]oxazol-3-one 2a. Moreover, an enantiodivergent synthesis of the pyrrolizidine alkaloids (+) and (-)-xenovenine was achieved starting from the same chiral building block 2a.