74745-63-4

Upstream product

• 219915-96-5 N¹-(4-methoxy-benzyl)-2-methyl-1-phenyl-propane-1,2-diamine 
• 219915-89-6 (4-methoxy-benzyl)-(2-methyl-2-nitro-1-phenyl-propyl)-amine 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 31490-38-7 N-(4-methoxybenzyl)benzaldimine 

Relevant academic research and scientific papers

The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines

The addition of alkyl nitronate anions to PMB imines, derived from benzaldehyde or straight-chain carbaldehydes, in the presence of a Bronsted acid, proceeds in greater than 90% yield with up to 10:1 diastereoselection favoring the anti isomer. The mechanism of this addition reaction is intriguing and is under investigation. The moderately unstable β-nitro amines can be reduced with samarium diodide and the PMB group removed with CAN, in good overall yields, to give sensitive 1,2-diamines without erosion of diastereoselectivity. This protocol represents a new, stereoselective synthesis of certain 1,2-diamines.