771476-39-2

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 722-04-3 N-(3-dimethylaminopropyl)-N’-phenylthiourea 
• 590-86-3 isovaleraldehyde 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 867061-70-9 (6R)-6-isopropyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine 
• 700869-00-7 (5R)-6-methyl-5-(N-phenyl-aminoxy)-hept-3-en-2-one 
• 608130-30-9 (R)-3-methyl-2-(N-phenyl-aminooxy)-butan-1-ol 

Relevant academic research and scientific papers

Organocatalytic Asymmetric Tandem α-Aminooxylation–Henry Reactions for the Synthesis of 1,2-Diols: Total Synthesis of (–)-l-threo-Sphinganine

A new and rapid asymmetric synthesis of anti- and syn-β,γ-dihydroxynitroalkanes through an organocatalytic tandem α-aminooxylation–Henry reaction is described. The target diol derivatives were synthesized in good yields, with excellent enantioselectivitie

Dual-organocatalyst-promoted asymmetric cascade reaction: Highly efficient construction of enantiopure fully substituted tetrahydro-1,2-oxazines

A four-component asymmetric α-aminoxylation/aza-Michael/Mannich cascade reaction for the construction of fully substituted chiral tetrahydro-1,2-oxazine derivatives was accomplished in high yields with excellent enantio- and diastereoselectivities under m

Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and α-aminoxy alcohols in a nonpolar medium

A proline-thiourea host-guest complex is described as a self-assembled organocatalyst for the enantioselective Michael addition of aldehydes to nitroolefins and for the asymmetric α-aminoxylation of both aldehydes and ketones. The Michael adducts were obt

Continuous proline catalysis via leaching of solid proline

Herein, we demonstrate that a homogeneous catalyst can be prepared continuously via reaction with a packed-bed of a catalyst precursor. Specifically, we perform continuous proline catalyzed α-aminoxylations using a packed-bed of L-proline. The system relies on a multistep sequence in which an aldehyde and thiourea additive are passed through a column of solid proline, presumably forming a soluble oxazolidinone intermediate. This transports a catalytic amount of proline from the packed-bed into the reactor coil for subsequent combination with a solution of nitrosobenzene, affording the desired optically active α-aminooxy alcohol after reduction. To our knowledge, this is the first example in which a homogeneous catalyst is produced continuously using a packedbed. We predict that the method will not only be useful for other L-proline catalyzed reactions, but we also foresee that it could be used to produce other catalytic species in flow.

Ionic-liquid tagged prolines as recyclable organocatalysts for enantioselective α-aminoxylations of carbonyl compounds

With the aim of improving catalytic performance and recyclability various ionic-liquid-tagged organocatalysts (ILTOCs) based on (S)-proline as organocatalysts and triazolium or guanidinium salts as ionic liquid tags were applied in the asymmetric α-aminox

Imidazolium ion-tagged proline organocatalyst for α-aminoxylation of aldehydes and ketones in ionic liquids

A novel imidazolium ion-tagged L-proline catalyst has been developed. The asymmetric α-aminoxylation of aldehydes and ketones with excellent enantioselectivities, up to 99% ee, and high yields in ionic liquids has been achieved. The system can be easily recycled and reused for at least six times without significant loss of yields and enantioselectivity.

Enantioselective synthesis of syn / anti -1,3-amino alcohols via proline-catalyzed sequential α-aminoxylation/α-amination and horner-wadsworth-emmons olefination of aldehydes

(Figure presented) A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential α-aminoxylation/ α-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5- phenylpentan-2-ol, is also accomplished.

Highly enantioselective l-thiaproline catalyzed α-aminoxylation of aldehydes in aqueous media

Highly enantioselective L-thiaproline catalyzed α-aminoxylation of aldehydes in the presence of water and tetrabutylammonium bromide followed by in situ reduction to afford the respective α-aminoxy alcohols has been developed in good to high yields (74-88%) and excellent enantioselectivities (93->99%).

Highly enantioselective α-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst

The first catalytic enantioselective α-aminoxylation of aldehydes and ketones using an insoluble, polymer-supported organocatalyst (1) derived from trans-4-hydroxyproline is reported (ee: 96-99%). Reaction rates in the aminoxylation of cyclic ketones with 1 are higher than those reported with L-proline. The insoluble nature of 1 simplifies workup conditions and allows catalyst recycling without an apparent decrease in enantioselectivity or yield.

Highly enantioselective α-aminoxylation of aldehydes and ketones in ionic liquids

As the first example for the synthesis of optically active α-hydroxyaldehydes and α-hydroxyketones in ionic liquids, we applied RTILs into L-proline catalyzed direct enantioselective α-aminoxylation of both aldehydes and ketones successfully. This protoco