173727-98-5Relevant articles and documents
Method for synthesizing chiral 1,2-diol compound
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Paragraph 0027; 0057-0060, (2021/07/21)
The invention relates to a method for synthesizing a chiral 1,2-diol compound, which comprises the following steps: sequentially adding a cobalt catalyst, a ligand, alpha-hydroxy ketone, an organic solvent and silane into a reaction system at 20-30 DEG C in a nitrogen atmosphere, then stirring the mixture, and carrying out column chromatography separation on the obtained product to obtain the chiral 1,2-diol compound. The high-yield cobalt catalyst in the earth crust is used, meanwhile, cheap silane (PMHS, 500 g/298 yuan) is used as a reducing agent, the asymmetric reduction reaction of alpha-hydroxy ketone can be efficiently achieved under the mild condition, and the chiral 1,2-diol compound with high yield and optical activity is obtained. Moreover, through the creative labor of the inventor, the reaction yield can reach 99%, and meanwhile, the content of the target product in the generated reaction product is 99% (namely, the yield is 99%, 99% ee).
Asymmetric hydrogenation of α-hydroxy ketones catalyzed by MsDPEN-Cp*Ir(III) complex
Ohkuma, Takeshi,Utsumi, Noriyuki,Watanabe, Masahito,Tsutsumi, Kunihiko,Arai, Noriyoshi,Murata, Kunihiko
, p. 2564 - 2567 (2008/02/05)
Asymmetric hydrogenation of a series of α-hydroxy aromatic ketones in methanol catalyzed by Cp*Ir(OTf)(MsDPEN) (MsDPEN = N-(methanesulfonyl)-1, 2-diphenylethylenediamine) affords the 1-aryl-1,2-ethanediols in up to 99% ee. The reaction can be conducted with a substrate-to-catalyst molar ratio at high as 6000 under 10 atm of H2-1-Hydroxy-2-propanone is also hydrogenated with high enantioselectivity.
Microbiological Transformations. 38. Clues to the Involvement of a General Acid Activation during Hydrolysis of Para-Substituted Styrene Oxides by a Soluble Epoxide Hydrolase from Syncephalastrum racemosum
Moussou,Archelas,Baratti,Furstoss
, p. 3532 - 3537 (2007/10/03)
In the course of this work, we have determined the regioselectivity as well as the rate of biohydrolysis of various para-substituted styrene oxide derivatives catalyzed by a new epoxide hydrolase activity found in the soluble cell extract of the fungus Syncephalastrum racemosum. We have observed that this regioselectivity switched progressively from the benzylic Cα carbon atom to the terminal Cβ carbon atom depending upon the electronic character of the para substituent. Hammett plotting of the ratio of water incorporation at both the benzylic and terminal carbon atoms, i.e., log α/β versus σ, gave linear relationships for the two (R)- and (S)-epoxide enantiomers with slopes pα/β = -2.07 and -1.35, respectively. Apparent kinetic constants Km and Vmax were determined for the biohydrolysis of the enantiomers of R absolute configuration, which were the better substrates. Hammett correlation was investigated for Vmax/Km for the reaction on both the Cα and Cβ carbon atoms. Log αVmax/Km vs σ gave a linear relationship with a slope pαvmax/Km = -1.8, suggesting that, in the case of these enzyme/substrate couples, the rate-determining step is the oxirane ring cleavage. These results give, for the first time, interesting clues to the fact that a general acid activation of the epoxide is very probably involved in a concerted process together with its nucleophilic attack.
