1936-63-6Relevant articles and documents
Montmorillonite-K10 catalyzed addition of trimethylsilylcyanide (TMSCN) to aldehydes
Somanathan,Rivero,Gama, Angeles,Ochoa,Aguirre
, p. 2043 - 2048 (1998)
Addition of trimethylsilyl cyanide (TMSCN) to aldehydes was catalyzed by Montmorillonite-K10, with subsequent reduction to β-aminoalcohol.
β-amino alcohol properfumes
Yang, Yongzheng,Wahler, Denis,Reymond, Jean-Louis
, p. 2928 - 2936 (2003)
Amino-alcohol derivatives of fragrant, volatile aldehydes and ketones were synthesized in a one-pot procedure by sequential cyanohydrin formation with trimethylsilyl cyanide and reduction with lithium aluminium hydride, or by ammonolysis of epoxide precursors. The amino alcohols are nonvolatile, stable properfumes releasing fragrant carbonyls by oxidation with sodium periodate or sodium bismuthate. Examples include amino alcohol properfumes of citronellal, Lilial, lauryl aldehyde, menthone, benzaldehyde, and anisaldehyde.
Asymmetric Sulfoxidation by Dopamine β-Hydrolase, an Oxygenase Heretofore Considered Specific for Methylene Hydroxylation
May, Sheldon W.,Phillips, Robert S.
, p. 5981 - 5983 (1980)
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Heterogenization of chiral mono oxazoline ligands by grafting onto mesoporous silica MCM-41 and their application in copper-catalyzed asymmetric allylic oxidation of cyclic olefins
Samadi, Saadi,Jadidi, Khosrow,Khanmohammadi, Behnam,Tavakoli, Niloofar
, p. 344 - 353 (2016)
A series of chiral 4-oxazolinylaniline ligands 8 were conveniently synthesized on a gram scale from inexpensive and commercially available 4-aminobenzoic acid in four steps. The obtained organic chiral ligands have been covalently grafted onto ordered mesoporous silicas MCM-41 and the resulting inorganic–organic hybrid materials have been characterized by thermogravimetric analysis (TGA), differential thermal analysis (DTA), powder X-ray diffraction, BET and BJH nitrogen adsorption–desorption methods, energy-dispersive X-ray spectroscopy (EDX), CHN analysis, scanning electron microscopy (SEM), and Fourier transform infrared spectroscopy (FT-IR). The catalytic and induced asymmetric effects of the chiral copper (I) complexes of these new chiral supported heterogeneous catalysts on the asymmetric allylic oxidation of cycloolefins were investigated under different conditions. Reactions using the catalyst exhibited moderate to good enantioselectivities, up to 80%, and good yields, up to 95% better than the corresponding homogeneous reaction. The catalyst could be recovered easily and reused five times without remarkable loss of reactivity, yield, or enantioselectivity. This is, to the best of our knowledge, the first heterogenization of chiral 4-oxazolinylaniline ligands on an inorganic (silica) surface and their application as a heterogeneous catalyst in the asymmetric Kharash–Sosnovsky reaction.
Overcoming thermodynamic and kinetic limitations of aldolase-catalyzed reactions by applying multienzymatic dynamic kinetic asymmetric transformations
Steinreiber, Johannes,Schuermann, Martin,Wolberg, Michael,Van Assema, Friso,Reisinger, Christoph,Fesko, Kateryna,Mink, Daniel,Griengl, Herfried
, p. 1624 - 1626 (2007)
(Figure Presented) Dynamic and successful: The asymmetric synthesis of 2-amino-1-phenylethanol was achieved by aminomethylation of benzaldehyde in the presence of the two enzymes L-threonine aldolase and L-tyrosine decarboxylase in a novel one-pot, two-enzyme process (see scheme). A modified method with three enzymes led to the enantioenriched amino alcohol in very high yield.
Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis
Sato, Eisuke,Fujii, Mayu,Tanaka, Hiroki,Mitsudo, Koichi,Kondo, Masaru,Takizawa, Shinobu,Sasai, Hiroaki,Washio, Takeshi,Ishikawa, Kazunori,Suga, Seiji
, p. 16035 - 16044 (2021/09/02)
Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.
Method for synthesizing chiral alpha-amino alcohol compound
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Paragraph 0026; 0053-0056, (2021/07/28)
The invention discloses a method for synthesizing a chiral alpha-amino alcohol compound. The method comprises the following steps: sequentially adding an iron catalyst, a ligand, ketone, an organic solvent and silane into a reaction system at 20-30 DEG C in a nitrogen atmosphere, then stirring the obtained mixture, and carrying out column chromatography separation on the obtained product to obtain a product, namely chiral alpha-amino alcohol. According to the invention, the most high-yield iron catalyst in earth crust is used, and cheap silane (PMHS, 500 g/298 yuan) is adopted as a reducing agent, so the asymmetric reduction reaction of alpha-amino ketone can be efficiently achieved under mild conditions so as to obtain the high-yield optically-active chiral alpha-amino alcohol compound; and moreover, through the creative labor of the inventor, reaction yield can reach 99%, and meanwhile, the content of the target product in the generated reaction product is 99%.
Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein
Cho, Inha,Prier, Christopher K.,Jia, Zhi-Jun,Zhang, Ruijie K.,G?rbe, Tamás,Arnold, Frances H.
, p. 3138 - 3142 (2019/02/01)
Chiral 1,2-amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable cytochrome c that directly transforms alkenes to amino alcohols with high enantioselectivity (up to 2500 TTN and 90 % ee) under anaerobic conditions with O-pivaloylhydroxylamine as an aminating reagent. The reaction is proposed to proceed via a reactive iron-nitrogen species generated in the enzyme active site, enabling tuning of the catalyst's activity and selectivity by protein engineering.
