- Synthesis method of gamma-or delta-substituted alkyl chiral lactone
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The invention discloses a synthesis method of gamma-or delta-substituted alkyl chiral lactone, the synthesis method comprises the following steps: mixing nickel salt, a chiral bidentate organic phosphorus ligand, aliphatic gamma-or delta-ketonic acid and a solvent, and carrying out asymmetric reduction reaction under the action of a reducing agent to obtain the gamma-or delta-substituted alkyl chiral lactone. According to the invention, asymmetric hydrogenation of aliphatic gamma-and delta-ketonic acids is realized through a cheap, green and efficient homogeneous chiral nickel-phosphorus complex catalytic system, and gamma-or delta-substituted alkyl chiral lactone is obtained with excellent yield and high enantioselectivity.
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Paragraph 0011; 0036-0039
(2022/03/17)
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- Chemo-enzymatic synthesis of optically active γ- and δ-decalactones and their effect on aphid probing, feeding and settling behavior
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The enantiomerically enriched γ- and δ-decalactones (4a and 4b) were prepared from corresponding racemic primary-secondary 1,4- and 1,5-diols (1a and 1b), as products of enzymatic oxidation catalyzed by different alcohol dehydrogenases. The results of biotransformations indicated that the oxidation processes catalyzed by alcohol dehydrogenase (HLADH), both isolated from horse liver and recombinant in Escherichia coli, were characterized by the highest degree of conversion with moderate enantioselectivity of the reaction. Useful, environmentally friendly extraction procedure of decalactones (4a and 4b) based on hydrodistillation using a Deryng apparatus was developed. Both racemic lactones (4a and 4b), as well as their enantiomerically enriched isomers, were tested for feeding deterrent activity against Myzus persicae. The effect of these compounds on probing, feeding and settling behavior of M. persicae was studied in vivo. The deterrent activity of decalactones (4a and 4b) against aphids depended on the size of the lactone ring and the enantiomeric purity of the compounds. δ-Decalactone (4b) appeared inactive againstM. persicae while γ-decalactone (4a) restrained aphid probing at ingestional phase. Only (-)-(S)-γ-decalactone (4a) had strong and durable (i.e. lasting for at least 24 hours) limiting effect, expressed at phloem level.
- Boratyński, Filip,Dancewicz, Katarzyna,Paprocka, Marlena,Gabrys?, Beata,Wawrzeńczyk, Czes?aw
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- Novozyme 435 asymmetric hydrolysis of enol ester with series acid moiety
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(R)-2-pentylcyclopentanone can be synthesized by the asymmetric hydrolysis of enol esters, catalyzed by immobilized candida antarctica (novozyme 435) lipase. Different acid moieties influence the stereoselectivity of lipase. Enol esters can be prepared fr
- Li, Quan,Jia, Weimin,Wang, Zhijian,Guo, Xiaodan
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p. 607 - 610
(2014/06/09)
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- A new environmentally benign catalytic process for the asymmetric synthesis of lactones: Synthesis of the flavouring δ-decalactone molecule
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The system Sn-Beta/hydrogen peroxide is applied to the Baeyer-Villiger oxidation of delfone to δ-decalactone, which is an industrial fragrance. The reaction is carried out without solvent and with a substrate/catalyst ratio > 200 (wt/wt). Starting with an enantiomerically enriched delfone it is shown that the rearrangement occurs with retention of configuration at the migrating asymmetric carbon atom, and enantiomerically enriched δ-decalactone is obtained as product. This process offers clear advantages over the actual industrial production that uses peracids as oxidants.
- Corma, Avelino,Iborra, Sara,Mifsud, Mari?a,Renz, Michael,Susarte, Manuel
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p. 257 - 262
(2007/10/03)
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- A facile synthesis of optically active lactones using benzyl-3,6-anhydro glucofuranoside as chiral auxiliary
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A highly enantioselective synthesis of γ- and δ-lactones using an anhydrofuranoside derived from D-glucose as chiral auxiliary is described.
- Nair, Vijay,Prabhakaran, Jaya,George, Tesmol G.
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p. 15061 - 15068
(2007/10/03)
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- Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C18 13-Hydroxy, C18 10-Hydroxy, and C19 14-Hydroxy Unsaturated Fatty Acids
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(S)-δ-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1).Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-γ-dodecanolide.When (S)-homocoriolic acid (3) was fed to C. suaveolens, γ-nonalide slightly enriched in the S enantiomer was produced.At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occured and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with deuterated 10 showed.
- Cardillo, Rosanna,Fronza, Giovanni,Fuganti, Claudio,Grasselli, Piero,Mele, Andrea,et al.
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p. 5237 - 5239
(2007/10/02)
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