915306-68-2

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 161661-47-8 (-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 
• 542-92-7 cyclopenta-1,3-diene 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 915306-63-7 (-)-(1S,3S,4R)-3-[(tert-butyldiphenylsiloxy)methyl]-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene 
• 915306-61-5 (-)-(1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-en-3-ylmethanol 

Downstream Products

• 915306-73-9 (+)-(2S,3S,5S)-2-[(tert-butyldiphenylsiloxy)methyl]-3,5-bis(hydroxymethyl)-1-[(1R)-1-phenylethyl]pyrrolidine 

Relevant academic research and scientific papers

Synthesis of polyhydroxylated pyrrolidines and aziridinopyrrolidines from [4π+2π] cycloadducts of cyclopentadiene and imines/2H-azirines

The synthesis of 2-functionalized 3,5-bis(hydroxymethyl)pyrrolidines from readily available polycyclic Diels-Alder adducts by a reaction sequence involving three steps is described. The same methodology has been applied to obtain the aziridine counter-par

Stereoselective synthesis of polyhydroxylated pyrrolidines: a route to novel 3,5-bis(hydroxymethyl)pyrrolidines from 2-azabicyclo[2.2.1]hept-5-enes

An efficient preparation of racemic and chiral 2-functionalized-3,5-bis(hydroxymethyl)pyrrolidines is described. The method uses 2-azabicyclo[2.2.1]hept-5-enes, readily obtained from glyoxylates of aliphatic amines and cyclopentadiene, as starting material. The hydroxylation of the double bond followed by the oxidative cleavage of the six-membered ring and in situ reduction of the dialdehyde intermediate gives the title pyrrolidines.