- Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions
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Aziridinium ions are useful reactive intermediates for the synthesis of enantiomerically enriched building blocks. However, N,N-dialkyl aziridinium ions are relatively underutilized in the synthesis of optically active molecules as compared to other three
- Chen, Yunwei,Sun, Xiang,Wu, Ningjie,Li, Jingbai,Jin, Shengnan,Zhong, Yongliang,Liu, Zirui,Rogachev, Andrey,Chong, Hyun-Soon
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p. 920 - 939
(2016/01/15)
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- PYRAZOLE INHIBITORS OF PHOSPHATIDYLINOSITOL 3-KINASE
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The present invention relates to compounds useful as inhibitors of PI3K, particularly of PI3Kγ. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of variou
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Page/Page column 17; 18
(2011/04/24)
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- Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol
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N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, β-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol.
- Duthion, Béranger,Métro, Thomas-Xavier,Gomez Pardo, Domingo,Cossy, Janine
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experimental part
p. 6696 - 6706
(2011/02/26)
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- Highly enantioselective synthesis of β-amino alcohols: A catalytic version
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(Chemical Equation Presented) Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of trifluoroacetic anhydride.
- Metro, Thomas-Xavier,Pardo, Domingo Gomez,Cossy, Janine
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p. 6556 - 6561
(2008/02/10)
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- Stereospecific rearrangement of β-amino alcohols catalyzed by H 2SO4
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Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of H2SO4. Georg Thieme Verlag Stuttgart.
- Métro, Thomas-Xavier,Pardo, Domingo Gomez,Cossy, Janine
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p. 2888 - 2890
(2008/02/12)
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- Highly enantioselective synthesis of β-amino alcohols
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N,N-Dialkyl-β-amino alcohols derived from α-amino acids can be rearranged enantiospecifically by using TFAA/Et3N/NaOH to give 1,2-amino alcohols with enantiomeric excess up to 99%.
- Metro, Thomas-Xavier,Appenzeller, Jerome,Pardo, Domingo Gomez,Cossy, Janine
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p. 3509 - 3512
(2007/10/03)
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- Combined ruthenium(II) and lipase catalysis for efficient dynamic kinetic resolution of secondary alcohols. Insight into the racemization mechanism
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Pentaphenylcyclopentadienyl ruthenium complexes (3) are excellent catalysts for the racemization of secondary alcohols at ambient temperature. The combination of this process with enzymatic resolution of the alcohols results in a highly efficient synthesis of enantiomerically pure acetates at room temperature with short reaction times for most substrates. This new reaction was applied to a wide range of functionalized alcohols including heteroaromatic alcohols, and for many of the latter, enantiopure acetates were efficiently prepared for the first time via dynamic kinetic resolution (DKR). Different substituted cyclopentadienyl ruthenium complexes were prepared and studied as catalysts for racemization of alcohols. Pentaaryl-substituted cyclopentadienyl complexes were found to be highly efficient catalysts for the racemization. Substitution of one of the aryl groups by an alkyl group considerably slows down the racemization process. A study of the racemization of (S)-1-phenylethanol catalyzed by ruthenium hydride η5-Ph5CpRu(CO) 2H (8) indicates that the racemization takes place within the coordination sphere of the ruthenium catalyst. This conclusion was supported by the lack of ketone exchange in the racemization of (S)-1-phenylethanol performed in the presence of p-tolyl methyl ketone (1 equiv), which gave 1% of 1-(p-tolyl)ethanol. The structures of ruthenium chloride and iodide complexes 3a and 3c and of ruthenium hydride complex 8 were confirmed by X-ray analysis.
- Martin-Matute, Belen,Edin, Michaela,Bogar, Krisztian,Kaynak, F. Betuel,Baeckvall, Jan-E.
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p. 8817 - 8825
(2007/10/03)
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- Optically active α-amino aldehydes, process for the preparation thereof, and the use thereof for the stereoselective preparation of optically active β-amino alcohols
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The invention relates to new optically active α-amino aldehydes of the formulae STR1 in which R1 represents an optionally substituted alkyl, alkenyl, aralkyl or aryl radical, and R2 and R3, independently of one another, denote an optionally substituted alkyl, alkenyl, cycloalkyl or aralkyl group, together form an optionally substituted phenylene-(1,2)-bis-methylene radical, or R2 is an optionally substituted, alkyl, cycloalkyl or aralkyl radical, and R3 forms together with R1 a 1,3-propylene radical. a process for the preparation thereof, and the use thereof for the stereoselective preparation of optically active β-amino alcohols.
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