545376-44-1

Upstream product

• 17851-97-7 1-tri(n-butyl)stannyloxy-1-cyclohexene 
• 586-96-9 Nitrosobenzene 
• 2981-10-4 1-(cyclohex-1-en-1-yl)piperidine 
• 108-94-1 cyclohexanone 
• 22780-11-6 1-(2,2,2-trichloroacetoxy)cyclohexene 

Downstream Products

• 53439-93-3 (S)-α-hydroxycyclohexanone 

Relevant academic research and scientific papers

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

Enantioselective nitroso aldol reaction catalyzed by quinoxp *silver(I) complex and tin methoxide

A catalytic enantioselective O-nitroso aldol reaction of alkenyl trichloroacetates with nitrosoarenes was achieved using the (R,R)-t-Bu- QuinoxP*AgOAc complex as the chiral catalyst and Bu2Sn(OMe) 2 as the achiral cocatalyst in the presence of methanol. Optically active ?-aminooxy ketones with up to 99% ee were regioselectively obtained in high yields from various alkenyl trichloroacetates of cyclic ketones.

Nonlinear effects in asymmetric amino acid catalysis by multiple interconnected stereoselective catalytic networks

A fine line: The generation of significant positive nonlinear effects in asymmetric amino acid catalysis under homogeneous conditions, which can be explained by the model for cooperative catalytic stereoselective pathways, is reported. The addition of an achiral aldehyde generated the multiple interconnected stereoselective catalytic network.

Enantioselectivity switch in direct asymmetric aminoxylation catalyzed by binaphthyl-based chiral secondary amines

Binaphthyl-based amino acids (S)-1 and an aminosulfonamide (S)-2 were applied for direct asymmetric aminoxylation with nitrosobenzene. In the presence of either (S)-1 or (S)-2, the aminoxylation of aldehydes proceeded smoothly, and subsequent reduction wi

Sugar-assisted kinetic resolution of amino acids and amplification of enantiomeric excess of organic molecules

The origins of biological homochirality have intrigued researchers since Pasteur's discovery of the optical activity of biomolecules. Herein, we propose and demonstrate a novel alternative for the evolution of homochirality that is not based on autocataly

PROCESS OF MAKING α-AMINOOXYKETONE/α-AMINOOXYALDEHYDE AND α-HYDROXYKETONE/α-HYDROXYALDEHYDE COMPOUNDS AND A PROCESS OF MAKING REACTION PRODUCTS FROM CYCLYC α,?-UNSATURATED KETONE SUBSTRATES AND NITROSO SUBSTRATES

The present invention is directed to a process of making α-aminooxyketone and α--hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of formula (IV), wherein X1-X3 represent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the α-aminooxyketone compound formed to the α-hydroxyketone compound. The present invention results in α-aminooxyketone and α-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol / Michael reaction. The substrates of this reaction are generally cyclic α,?-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic α,?-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis

Two types of chiral Bronsted acid catalysts have been shown to catalyze regio- and enantioselective nitroso aldol synthesis between nitrosobenzene and achiral enamine. The combination of Bronsted acidity and amine moiety of enamine realizes complete regioselectivity with high enantioselectivity. After a survey of Bronsted acid catalysts, 1-naphthyl glycolic acid is found to be optimal in the O-nitroso aldol pathway, while 1-naphthyl TADDOL is the best catalyst for the N-nitroso aldol pathway. This is based on our finding on the control of regioselectivity by changing the amine moiety of enamine and the choice of Bronsted acidity. Copyright

Catalytic enantioselective synthesis of α-aminooxy and α-hydroxy ketone using nitrosobenzene

The highly enantioselective and O-selective nitroso aldol reaction of tin enolates 2 and nitrosobenzene (1) has been developed with the use of (R)-BINAP-silver complexes as a catalyst. After the various silver salts were surveyed, the AgOTf and the AgClO4 complex were found to be optimal in the O-selective nitroso aldol reaction in both asymmetric induction (up to 97% ee) and regioselection (O/N = >99/1), affording aminooxy ketone 3. The product 3 can be transformed to α-hydroxy ketone 5 without any loss of enantioselectivity. Thus, the method provides an efficient approach to the catalytic enantioselective introduction of oxygen α- to the carbonyl group. Copyright