890903-28-3Relevant academic research and scientific papers
Direct asymmetric N-specific reaction of nitrosobenzene with aldehydes catalyzed by a chiral primary amine-based organocatalyst
Qin, Long,Li, Lei,Yi, Lei,Da, Chao-Shan,Zhou, Yi-Feng
, p. 527 - 533 (2012/01/11)
Nitroso compounds have two reactive nitrogen and oxygen atoms. It is interesting and important to perform a nitrogen or oxygen selective reaction with interesting substrates. These atom specific reactions are crucial to specifically synthesis of specific compounds. An enantioselective N-specific reaction of nitrosobenzene with unmodified aldehydes was successfully achieved catalyzed first by a variety of primary amine-based organocatalysts with higher yield and enantioselectivity. The bulkier substituted groups of the organocatalyst and two hydrogen bonds from the organocatalyst and the oxygen atom of nitrosobenzene make the reaction preferentially N-specific and predominantly afford R products.
Bronsted acid assisted regio- and enantioselective direct o-nitroso aldol reaction catalysed by α,α-diphenylprolinol trimethylsilyl ether
Mielgo, Antonia,Velilla, Irene,Gomez-Bengoa, Enrique,Palomo, Claudio
supporting information; experimental part, p. 7496 - 7502 (2010/08/20)
In the presence of p-nitrobenzoic acid, the O-nitroso aldol reaction of nitrosobenzene with enolisable aldehydes may be promoted by commercially available α,α-diphenylprolinol trimethylsilyl ether. The reaction proceeds with good yields and essentially complete enantioselectivity, with catalyst loadings in the 510 mol % range. The resulting α-oxyaldehyde adducts may be transformed in situ into α-oxyimines, which provide 1,2-amino alcohols upon treatment with Grignard reagents, in good overall yield (45-59%) and with typical diastereomeric ratios ≥ 95:5.
Regio- and enantioselective direct oxyamination reaction of aldehydes catalyzed by α,α-diphenylprolinol trimethylsilyl ether
Palomo, Claudio,Vera, Silvia,Velilla, Irene,Mielgo, Antonia,Gomez-Bengoa, Enrique
, p. 8054 - 8056 (2008/09/18)
(Chemical Equation Presented) Donors not required: External hydrogen-bond donors are not required for a highly regio- and enantioselective oxyamination reaction of aldehydes with nitrosobenzene (see scheme). The reaction proceeds in the presence of the st
Direct asymmetric hydroxyamination reaction catalyzed by an axially chiral secondary amine catalyst
Kano, Taichi,Ueda, Mitsuhiro,Takai, Jun,Maruoka, Keiji
, p. 6046 - 6047 (2007/10/03)
A direct asymmetric hydroxyamination reaction of aldehydes with nitrosobenzene was found to be catalyzed by the novel axially chiral secondary amine catalyst (S)-1d. The resulting optically enriched hydroxyamination products were readily converted to β-am
