1376622-75-1

Upstream product

• 14429-03-9 (R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine 
• 1376622-69-3 tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate 

Downstream Products

• 1376622-85-3 (R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine 
• 1376622-86-4 (R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-acetoxy-4-benzyloxy-5-methylpyrrolidine 
• 1376622-89-7 (R,R,R,R)-2-(4'-methoxyphenyl)-3-acetoxy-4-benzyloxy-5-methylpyrrolidine 
• 1376622-78-4 C₂₇H₃₁NO₃ 

Relevant academic research and scientific papers

Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: Application to the asymmetric synthesis of (-)-codonopsinine

Ring-closing iodoamination of (E)-configured, N-α-methyl-p- methoxybenzyl protected homoallylic amines upon treatment with I2 and NaHCO3 in MeCN occurs with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr.