- 1-acenaphthenol synthesis and enantiomer separation method
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The invention discloses a 1-acenaphthenol synthesis and enantiomer separation method. The method particularly comprises the following steps that 1-acenaphthenone serves as a raw material, catalytic reduction hydrogenation can be conducted through a catalyst to obtain racemic 1-acenaphthenol, the racemic 1-acenaphthenol is subjected to dynamic kinetic splitting and then separated to obtain an R-1-acenaphthenol acyl compound and S-1-acenaphthenol, the 1-acenaphthenol is subjected to dynamic kinetic splitting, only an R-1-acenaphthenol acyl compound is obtained, the R-1-acenaphthenol acyl compound obtained through kinetic splitting or dynamic kinetic splitting is hydrolyzed, and then R-1-acenaphthenol can be obtained. The method has the advantages of being easy to implement, high in product yield, good in optical purity and the like, and great guidance and application value is achieved in 1-acenaphthenol synthesis and splitting research.
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Paragraph 0014
(2017/08/27)
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- Selective acetylation of primary alcohols by ethyl acetate
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A KOtBu and ethyl acetate mediated efficient methodology has been developed for the acetylation of primary and secondary alcohols where ethyl acetate is the source of acetyl group. The reaction is fast, mild, efficient, and highly selective towards the primary alcohols.
- Singha, Raju,Ray, Jayanta K.
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supporting information
p. 5395 - 5398
(2016/11/11)
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- A green route to enantioenriched (S)-arylalkyl carbinols by deracemization via combined lipase alkaline-hydrolysis/Mitsunobu esterification
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Herein we report results of the chemoenzymatic deracemization of a range of secondary benzylic acetates 1a-9a via a sequence of hydrolysis with CAL-B lipase in non-conventional media, combined with esterification of the recovered alcohol according to the Mitsunobu protocol following an enzymatic kinetic resolution (KR). The KR of racemic acetates 1a-9a via an enzymatic hydrolysis, with CAL-B lipase and Na2CO3, in non-aqueous media was optimized and gave high selectivities (E ? 200) at good conversions (C >49%) for all of the substrates studied. This method competes well with the traditional one performed in a phosphate buffer solution. The deracemization using Mitsunobu inversion gave the (S)-acetates in moderate to excellent enantiomeric excess 75% ee 99%, in acceptable isolated yields 70% yield 89%, and with some variations according to the acetate structure.
- Houiene, Zahia,Merabet-Khelassi, Mounia,Bouzemi, Nassima,Riant, Olivier,Aribi-Zouioueche, Louisa
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p. 290 - 296
(2013/04/23)
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- Green methodology for enzymatic hydrolysis of acetates in non-aqueous media via carbonate salts
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Herein we report a new approach to enantiomerically enriched acetates using a lipase-catalyzed hydrolysis in non-aqueous media by alkaline carbonate salts. The use of sodium carbonate in the enzymatic hydrolysis with Candida antarctica lipase B (CAL-B) of racemic acetates shows a large enhancement of the reactivity and selectivity of this lipase. The role of the carbonate salts, the amount and the nature of the alkaline earth metal on the efficiency of this new pathway are investigated. The enzymatic kinetic resolution of acetates 1a-9a, by enzymatic-carbonate hydrolysis under mild conditions is described. In all cases, the resulting alcohols and remaining acetates were obtained in high ee values (up to >99%) while the selectivities reached E >500.
- Merabet-Khelassi, Mounia,Houiene, Zahia,Aribi-Zouioueche, Louisa,Riant, Olivier
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experimental part
p. 828 - 833
(2012/09/25)
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- Combined lipase-catalyzed resolution/Mitsunobu esterification for the production of enantiomerically enriched arylalkyl carbinols
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Several arylalkyl carbinols [1-indanol, 1-tetralol, 1-phenylethanol, 1-(1-naphthyl)ethanol, 1-(2-naphthyl)ethanol, 1-(4-methoxyphenyl)ethanol, 1-acenaphthenol] were deracemized through sequential combinations of lipase-catalyzed resolution and Mitsunobu inversion. The corresponding (R)-acetates were obtained in 72-83% yield and 89-99% ee.
- Bouzemi, Nassima,Aribi-Zouioueche, Louisa,Fiaud, Jean-Claude
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p. 797 - 800
(2007/10/03)
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- On the use of succinic anhydride as acylating agent for practical resolution of aryl-alkyl alcohols through lipase-catalyzed acylation
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A comparison is carried out of the E-values recorded in the lipase-catalyzed resolution of a series of secondary aryl-alkyl alcohols with enol esters versus succinic anhydride. Whereas all the substrates could be resolved by a proper choice of the lipase/enol ester couple with moderate (E=50) to good (E>100) enantioselectivities, only some of them showed satisfactory enantioselectivity (E>50) with the use of succinic acid as acylating agent. Notably, indanol and 1-quinolin-3-yl-ethanol were resolved in a practical way, with E>100 and E>80, respectively.
- Bouzemi, Nassima,Debbeche, Hanane,Aribi-Zouioueche, Louisa,Fiaud, Jean-Claude
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p. 627 - 630
(2007/10/03)
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- Kinetic resolution of 1-acenaphthenol and 1-acetoxynaphthene through lipase-catalyzed acylation and hydrolysis
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Acenaphthenyl acetate and acenaphthenol are resolved through Pseudomonas fluorescens lipase (PFL)-catalyzed hydrolysis and acylation, respectively. By contrast, the structurally related 1-(1-naphthyl)ethyl acetate and 1-(1- naphthyl)ethanol are inactive under the same reaction conditions. (C) 2000 Elsevier Science Ltd.
- Aribi-Zouioueche, Louisa,Fiaud, Jean-Claude
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p. 4085 - 4088
(2007/10/03)
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- Palladium-Catalyzed Substitution of Esters of Naphthylmethanols, 1-Naphthylethanols, and Analogues by Sodium Dimethyl Malonate. Stereoselective Synthesis from Enantiomerically Pure Sbstrates.
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The palladium-catalyzed substitution of carbonates of the titled alcohols was performed at lower temperature than the previously reported reaction of the corresponding acetates.The use of enantiomerically pure carbonates gave substitution products with overall retention of the configuration (up to 97 percent).
- Legros, Jean-Yves,Toffano, Martial,Fiaud, Jean-Claude
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p. 3235 - 3246
(2007/10/02)
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