138810-08-9

Upstream product

• 135697-21-1 (S)-(1-tert-butoxycarbonyl-5-oxopyrrolidin-2-yl)-methyl-4-methylbenzenesulfonate 
• 21395-93-7 (R)-(+)-5-methyl-2-pyrrolidinon 
• 14498-39-6 2-(1-Hydroxypropyl)-5-methylpyrrolidine 
• 138722-99-3 (R)-3-(5-Methyl-2-pyrrolidinylidene)furan-2-one 
• 138722-97-1 (R)-2-(1-Hydroxypropyl)-5-methyl-5H-3,4-dihydropyrrole 
• 138722-98-2 (R)-5-methoxy-2-methyl-3,4-dihydro-2H-pyrrole 
• 51693-17-5 (S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester 
• 29266-73-7 (-)-(S)-5-iodomethyl-2-pyrrolidinone 
• 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 

Downstream Products

• 138723-03-2 (2S,5R)-1-(Carbobenzyloxy)-2-(3-oxodecyl)-5-methylpyrrolidine 
• 138723-02-1 (2S,5R)-1-(Carbobenzyloxy)-2-(3-hydroxydecyl)-5-methylpyrrolidine 
• 138723-01-0 (2S,5R)-1-(Carbobenzyloxy)-2-(1-oxopropyl)-5-methylpyrrolidine 

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.