682746-16-3

Upstream product

• 586-96-9 Nitrosobenzene 
• 78-93-3 butanone 
• 186581-53-3 diazomethane 
• 123-38-6 propionaldehyde 

Downstream Products

• 909789-45-3 (6R)-5,6-dimethyl-2-phenyl-3,6-dihydro-2H-1,2-oxazine 

Relevant academic research and scientific papers

Direct catalytic enantioselective α-aminoxylation of ketones: A stereoselective synthesis of α-hydroxy and α,α′- dihydroxy ketones

Proline-catalyzed reactions between unmodified ketones and nitrosobenzene proceed with excellent diastereo- and enantioselectivities to provide protected α-hydroxy and α,α′-dihydroxy ketones [Eq. (1)]. Such compounds with chiral α-hydroxy carbonyl units are crucial in natural product synthesis.

Asymmetric synthesis of 3-hydroxyl-2-alkanones via tandem organocatalytic aminoxylation of aldehydes and chemoselective diazomethane homologation

Asymmetric synthesis of 3-hydroxyl-2-alkanones is achieved via one-pot, tandem organocatalytic aminoxylation of aldehydes and chemoselective CH2N2-induced homologation. Accelerating effect of water is observed in α-aminoxylation. MgC

A highly selective, organocatalytic route to chiral 1,2-oxazines from ketones

A sequential, organocatalysed asymmetric reaction to access chiral 1,2-oxazines from achiral ketone starting materials is reported, which proceeds in moderate to good yields and excellent enantioselectivity. The Royal Society of Chemistry 2006.

Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones

The direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording α-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (-20 °C) was found to be a key for the successful α-aminoxylation of aldehydes, while slow addition of nitrosobenzene is essential for that of ketones. The scope of the reaction is presented.

Direct proline-catalyzed asymmetric α-aminoxylation of ketones

Nitrosobenzene is the oxygen source in the direct catalytic enantioselective α-aminoxylation of ketones catalyzed by L-proline [Eq. (1)]. Versatile α-aminoxylated ketones are obtained in high yield and with excellent enantioselectivities.

The direct catalytic asymmetric α-aminooxylation reaction: Development of stereoselective routes to 1,2-diols and 1,2-amino alcohols and density functional calculations

Proline-catalyzed direct asymmetric α-aminooxylation of ketones and aldehydes is described. The proline-catalyzed reactions between unmodified ketones or aldehydes and nitrosobenzene proceeded with excellent diastereo- and enantioselectivities. In all cases tested, the corresponding products were isolated with > 95% ees. Methyl alkyl ketones were regiospecifically oxidized at the methylene carbon atom to afford enantiomerically pure α-aminooxylated ketones. In addition, cyclic ketones could be α,α′-dioxidized with remarkably high selectivity, furnishing the corresponding diaminooxylated ketones with > 99% ees. The reaction mechanism of the proline-catalyzed direct asymmetric α-aminooxylation was investigated, and we performed density functional theory (DFT) calculations in order to investigate the nature of the plausible transition states further. We also screened other organocatalysts for the asymmetric α-oxidation reaction and found that several proline derivatives were also able to catalyze the transformation with excellent enantioselectivities. Moreover, stereoselective routes for the synthesis of monoprotected vicinal diols and hydroxyketones were found. In addition, short routes for the direct preparation of enantiomerically pure epoxides and 1,2-amino alcohols are presented. The direct catalytic α-oxidation is also a novel route for the stereoselective preparation of β-adrenoreceptor antagonists.