197229-64-4

Upstream product

• 501-53-1 benzyl chloroformate 
• 132959-53-6 (2S)-2-(2-propenyl)pyrrolidine 
• 399044-21-4 N-[(1,1-dimethylethoxy)carbonyl]-2-(2-propen-1-yl)pyrrolidine 
• 132959-50-3 (5S)-allyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one 
• 82259-09-4 (5S)-(+)-5-(1-Prop-2-enyl)-2-pyrrolidinone 

Downstream Products

• 197230-40-3 (2S-(2S))-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)pyrrolidine 
• 197230-38-9 (2S-(2R))-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)pyrrolidine 
• 143771-09-9 (R)-2-(4-Oxo-heptyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 197230-44-7 (2S-(2R))-1-benzyloxycarbonyl-2-(2,3-epoxypropyl)pyrrolidine 
• 197230-46-9 (2S-(2S))-1-benzyloxycarbonyl-2-(2,3-epoxypropyl)pyrrolidine 
• 1016669-64-9 (2S)-benzyl 2-((E)-4-hydroxyhept-2-enyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine

(Chemical Equation Presented) The s-BuLi complex of a cyclohexane-derived diamine is as efficient as s-BuLi/(-)-sparteine for the asymmetric deprotonation of N-Boc pyrrolidine. This is the first example of high enantioselectivity using a non-sparteine-like diamine in such reactions. The ( S, S)-diamine is a useful (+)-sparteine surrogate and was utilized in short syntheses of (-)-indolizidine 167B and an intermediate for the synthesis of the CCK antagonist (+)-RP 66803.

Expedient syntheses of indolizidines (-)-167B and (-)-209D

Indolizidine alkaloids (-)-167B and (-)-209D were synthesized via an expedient route using hydroacylation and amination.

New synthesis of all the four isomers of 2-(2-hydroxypropyl)pyrrolidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement

Both enantiomers of 2-(2-propenyl)pyrrolidine 7 (75-84% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 5, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)pyrrolidines 8 with enantiomeric enhan