38382-25-1

Upstream product

• 108-94-1 cyclohexanone 
• 586-96-9 Nitrosobenzene 
• 17851-97-7 1-tri(n-butyl)stannyloxy-1-cyclohexene 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 22780-11-6 1-(2,2,2-trichloroacetoxy)cyclohexene 
• 227014-39-3 C₁₁H₂₄OSi₂ 

Relevant academic research and scientific papers

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

Thieme Chemistry Journal awardees - Where are they now? Dibutyltin dimethoxide catalyzed N-nitrosoaldol reaction of alkenyl trichloroacetate

Nitrosoaldol reaction between alkenyl trichloroacetates and nitrosobenzene has been achieved using dibutyltin dimethoxide as a catalyst, which is regenerated in the presence of methanol. The corresponding α-hydroxyamino ketones (N-adducts) have exclusivel

Simple synthesis of α-hydroxyamino carbonyl compounds: New scope of the nitroso aldol reaction

(graph presented) The reaction of nitroso compounds with enolates, the nitroso aldol reaction , occurs in high yield to generate α-hydroxyamino carbonyl compounds. Yields range from 42% to 98% with N-selectivity >99:1 from commercially available aromatic or aliphatic nitroso compounds and a variety of alkali metal or tin enolates.

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.

Enantioselective O-nitroso aldol reaction of silyl enol ethers

(Chemical Equation Presented) New nucleophiles for the O-nitroso aldol reaction in the form of readily prepared disilanyl enol ethers make this transformation more practicaland more versatile. A silver catalyst with a chiral biaryl phosphite ligand promotes the title reaction with high enantio- and regioselectivity (see scheme). R1,R2 = H, Ar; TMS = trimethylsilyl.