523987-31-7

Upstream product

• 523987-30-6 allyl N-benzyloxycarbonyl-trans-4-(allyloxy)-L-prolinate 
• 106-95-6 allyl bromide 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 1215232-81-7 (2S,4R)-dibenzyl 4-(allyloxy)pyrrolidine-1,2-dicarboxylate 
• 1369629-35-5 (2S,4R)-benzyl 4-(allyloxy)-2-carbamoylpyrrolidine-1-carboxylate 
• 1369629-37-7 (2S,4R)-benzyl 4-(allyloxy)-2-cyanopyrrolidine-1-carboxylate 
• 1369629-39-9 (2S,4R)-benzyl 4-(allyloxy)-2-(1H-tetrazol-5-yl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

A recyclable and highly stereoselective multi-fluorous proline catalyst for asymmetric aldol reactions

A recyclable fluorous proline catalyst with high stereoselectivity that functions as a catalyst for asymmetric aldol reactions is described. Its high stereoselectivity and facile recovery are achieved by employing a multi-fluorous tag attachment strategy. Although a gradual decrease was observed with respect to the catalytic activity, the catalyst can be separated from the reaction mixture by adsorption onto FluoroFlash and can be reused in that form for a maximum of five times while maintaining a high stereoselectivity.2019 Elsevier Ltd. All rights reserved.

Chemoselective synthesis of N-protected alkoxyprolines under specific solvation conditions

N-Protected hydroxyprolines (Hyp) were transformed chemoselectively into alkoxyproline derivatives by direct O-alkylation. The starting Hyp was transformed into the corresponding dianion in a mixture of dimethyl sulfoxide and tetrahydrofuran (1:16 v/v) as solvent. Under these conditions, the carboxy-anion showed reduced nucleophilicity because it was specifically solvated, and the more reactive oxy-anion was selectively alkylated. N-Protected trans-4-alkoxy-, cis-4-alkoxy- and trans-3-alkoxyprolines were thus obtained in a single step in very high overall yields and with complete stability of the stereogenic center configuration. Copyright

Synthesis and applications of the first polyfluorous proline derivative

Starting from trans-4-hydroxy-L-proline, a polyfluorinated proline derivative having a fluorine content of 54% has been prepared. It has been tested as a catalyst in the aldol reaction between p-nitrobenzaldehyde and acetone with 73% ee in BTF and in copper(I)-catalyzed allylic oxidation of cyclohexene with 20% ee in HFIP.