771476-46-1Relevant academic research and scientific papers
Enantioselectivity switch in direct asymmetric aminoxylation catalyzed by binaphthyl-based chiral secondary amines
Kano, Taichi,Yamamoto, Akihiro,Shirozu, Fumitaka,Maruoka, Keiji
, p. 1557 - 1563 (2009)
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
Stereodivergent approach to Alzheimer's therapeutic agent (R)-(?) and (S)-(+)-arundic acid employing chiral 4-pentenol derivatives as building blocks
Bhosale, Viraj A.,Waghmode, Suresh B.
, p. 2342 - 2348 (2017/04/03)
An efficient stereodivergent total synthesis of anti-Alzheimer agent (R)-(?) and (S)-(+)-arundic acid has been achieved from both chiral and nonchiral materials. This strategy features an efficient approach to separable diastereomeric C-2 chiral 4-pentenol intermediates employing proline catalysed asymmetric α-aminooxylation and [3,3] sigmatropic Claisen rearrangement are the highlights of present synthesis.
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
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.
Direct asymmetric aminoxylation reaction catalyzed by a binaphthyl-based chiral amino sulfonamide with high catalytic performance
Kano, Taichi,Yamamoto, Akihiro,Maruoka, Keiji
, p. 5369 - 5371 (2008/12/21)
A binaphthyl-based amino sulfonamide (S)-2 was applied to the direct asymmetric aminoxylation of aldehydes with nitrosobenzene. The reaction catalyzed by (S)-2 proceeded smoothly to give the aminoxylated product in good yield with excellent enantioselectivity. This method represents a rare example of the highly enantioselective aminoxylation by a non-proline type catalyst with high catalytic performance.
