180747-36-8

Upstream product

• 17061-62-0 N,N-bis(p-methoxybenzyl)amine 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 880175-70-2 (2R,3S)-N,N-bis(4-methoxybenzyl)-3-phenyl-2-oxiranecarboxamide 

Relevant academic research and scientific papers

Highly stereoselective intramolecular Buchner reaction of diazoacetamides catalyzed by a Ru(ii)-Pheox complex

This work reports the first efficient enantioselective intramolecular Buchner reaction of diazoacetamides. The Ru(ii)-Pheox catalyst was shown to be highly efficient in this transformation in terms of both the regio-and enantioselectivity (up to 99% ee) giving the desired products in quantitative yield.

Catalytic Enantioselective Intramolecular C(sp3)?H Amination of 2-Azidoacetamides

An enantioselective ring-closing C(sp3)?H amination of 2-azidoacetamides is catalyzed by a chiral-at-metal ruthenium complex and provides chiral imidazolidin-4-ones in 31–95 % yield, with enantioselectivities of up to 95 % ee, and at catalyst loadings down to 0.1 mol % (turnover number (TON)=740). To our knowledge, this is the first example of a highly enantioselective C(sp3)?H amination with aliphatic azides. Mechanistic experiments reveal the importance of the amide group, which presumably enables initial bidentate coordination of the 2-azidoacetamides to the catalyst. DFT calculations show that the transition state leading to the major enantiomer features a better steric fit and favorable π–π stacking between the substrate and the catalyst framework.

Samarium(II) iodide mediated intermolecular coupling reactions of N,N-dibenzyl-α-haloamides with carbonyl compounds

Samarium(II) iodide mediated coupling reactions of α-haloamides with carbonyl compounds are found to give N,N-dibenzyl-β-hydroxyamides (4a-i, 5a-i, and 6a) in good yields under mild reaction conditions. The transformation of 4a and 5a to N,N-dibenzyl-3-phenylpropanamide (7) and β-hydroxycarboxylic acid (8), respectively, are described.