431887-13-7

Upstream product

• 431887-12-6 (3aR,7aR,7bR,8aR)-7b-phenyldecahydro-3b,4a-diazadicyclopenta[a,e]pentalen-4-one 
• 431887-10-4 (all-R)-tert-butyl-2-(2-oxo-2-phenylethyl)cyclopentyl carbamate 
• 349558-27-6 (all-R)-N-(tert-Butyloxycarbonyl)-2-azabicyclo[3.3.0]octan-3-one 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 96446-97-8 (all-R)-2-phenyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrole 

Relevant academic research and scientific papers

Highly diastereoselective addition of N-Boc-pyrrolidin-2-yllithium to optically active ketimines - Synthesis of enantiomerically pure 1,3-imidazolidin-2-ones and diamines

A highly diastereoselective addition of chiral N-Boc-pyrrolidin-2-yllithium to optically active bicyclic ketimines has been developed. For this purpose alkyl- and aryl-substituted chiral N-Boc-amino ketones 2 have been synthesized by addition of various Grignard reagents to an N-Boc-protected lactam 1. The resulting N-Boc-amino ketones 2 have been converted into bicyclic ketimines 3 after deprotection and intramolecular cyclization. A kinetic resolution of the racemic organolithium compound by the chiral substrate is discussed based on X-ray crystal structure analysis and experimental results. The influence of the substituent of the ketimine has been studied. Some of the obtained tetracyclic 1,3-imidazolidin-2-ones 4 have been converted into tetracyclic aminals 5 and these compounds have been hydrolysed to the desired diamines 6.