771476-36-9

Upstream product

• 123-38-6 propionaldehyde 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 757960-84-2 O-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-N-phenyl-hydroxylamine 
• 608130-28-5 (R)-2-(N-phenylaminoxy)propan-1-ol 

Relevant academic research and scientific papers

The direct and enantioselective organocatalytic α-oxidation of aldehydes

The first direct enantioselective catalytic α-oxidation of carbonyls has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective oxyamination of aldehydes, to generate α-oxyaldehydes, important chiral synthons for natural product and medicinal agent synthesis. The use of l-proline as the asymmetric catalyst has been found to mediate the oxidation of a large variety of aldehyde substrates with nitrosobenzene serving as the electrophilic oxidant. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 2 mol % were generally employed in this study, successful oxidations conducted using catalyst loadings as low as 0.5 mol % are described. Copyright

Amplification of enantiomeric excess in a proline-mediated reaction

The evolution of homochirality from simple organic molecules can perhaps be modeled on the proline-mediated aminoxylation of aldehydes (see scheme). The observed accelerating reaction rate combined with an amplification of the enantiomeric excess of the product is attributed to an autoinductive reaction mediated by an adduct of proline and the product.

One-pot preparation of ethyl 2(Z)-4-(anilinoxy)-pentenoate by α-aminoxylation of propanal followed by Z-selective HWE reaction and the study on its cyclization reaction

A one-pot sequence of α-aminoxylation of n-propanal catalyzed by L-proline followed by the Z-selective Horner-Wadsworth-Emmons reaction was developed. The highly functionalized chiral γ-anilinoxy-Z-α,β-unsaturated ester 6 was obtained in 57-58% yield with 98:2 Z-selectivity from n-propanal in one-pot procedure. The transformation of the anilinoxy group of 6 into a hydroxyl group can be carried out by treatment with catalytic amount of CuSO4 in methanol to give either the corresponding alcohol 8 or chiral γ-valerolactone 4a in moderate yield. Chiral 6-methyl-2-phenyl-2H-1,2-oxazin-3(6H)-one 7 was obtained in 75% yield from 6 by treatment with CSA.

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

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

PROCESSES OF ENANTIOSELECTIVELY FORMING AN AMINOXY COMPOUND AND AN 1,2-OXAZINE COMPOUND

Disclosed is a process of enantioselectively forming an aminoxy compound of Formula (3) In formula (3) R1 is one of an aliphatic group and an alicyclic group. R2 is one of hydrogen, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group and an arylalicyclic group. R3 is one of hydrogen, halogen, hydroxyl, and an aliphatic group with a main chain having 1 to about 10 carbon atoms. The respective aliphatic, alicyclic, aromatic, arylaliphatic or arylalicyclic groups of R1, R2, and R3 comprise 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. The process includes contacting a carbonyl compound of Formula (1) and a nitroso compound of Formula (2) in the presence of a chiral catalyst. The chiral catalyst is a compound of Formula (IX)

Cyclic carbonates as sustainable solvents for proline-catalysed aldol reactions

Ethylene and propylene carbonates, which can be prepared from epoxides and carbon dioxide, are effective solvents for the proline-catalysed, 100% atom economical, asymmetric aldol reaction between enolisable and non-enolisable carbonyl compounds. The opti

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.

A coherent mechanistic rationale for additive effects and autoinductive behaviour in proline-mediated reactions

Differences in the kinetic behaviour of aldol reactions compared to aminoxylation and amination reactions are rationalized by consideration of the rate-determining step in each case. Both autoinductive behaviour and the rate-enhancing effect of additives

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%).