85617-05-6Relevant academic research and scientific papers
Enzymatic chemical transformations of aldehydes, ketones, esters and alcohols using plant fragments as the only biocatalyst: Ximenia americana grains
da Silva, Romézio Alves Carvalho,de Mesquita, Bruna Marques,de Farias, Iolanda Frota,do Nascimento, Patrícia Georgiana Garcia,de Lemos, Telma Leda Gomes,Queiroz Monte, Francisco José
, p. 187 - 194 (2018/01/05)
The present study demonstrated the ability of Ximenia american as a biocatalyst in reduction, hydrolysis and esterification reactions. The reduction reactions of aldehydes and ketones, ester hydrolysis and esterification of alcohols were carried out with interesting results. Reduction of ketones afforded yields of 6–60% with ee in the range of 35–>99% and that of aldehydes in yields of 51–99%. On the other hand, ester hydrolysis afforded yields of 58–98% with ee in the range 34–87%, while esterification of alcohols in 18–99% yields. Experimental conditions for all reactions have been defined using standard substrates as indicated in results and discussion. Some of the products are the potential building blocks for the synthesis of molecules which are of pharmaceutical and agrochemical importance.
Chiral surfactant-type catalyst for asymmetric reduction of aliphatic ketones in water
Li, Jiahong,Tang, Yuanfu,Wang, Qiwei,Li, Xuefeng,Cun, Linfeng,Zhang, Xiaomei,Zhu, Jin,Li, Liangchun,Deng, Jingen
supporting information, p. 18522 - 18525 (2013/01/15)
A novel chiral surfactant-type catalyst is developed. Micelles formed in water by association of the catalysts themselves, and this was confirmed by TEM analyses. Asymmetric transfer hydrogenation of aliphatic ketones catalyzed by the chiral metallomicellar catalyst gave good to excellent conversions and remarkable stereoselectivities (up to 95% ee). Synergistic effects between the metal-catalyzed center and the hydrophobic microenvironment of the core in the metallomicelle led to high enantioselectivities.
Stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol and its propionate, the sex pheromones of pine sawflies
Kovalenko, Vitaly,Matiushenkov, Evgenii
, p. 1393 - 1399,7 (2020/09/16)
The stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol (diprionol) and its propionate, the sex pheromones of pine sawflies (Neodiprion sp. and other), in high enantiomeric purity was achieved from (1R,3S)-2,2-dichloro-3-methylcyclopropane
Reduction processes biocatalyzed by Vigna unguiculata
Bizerra, Ayla M.C.,Gonzalo, Gonzalo de,Lavandera, Ivan,Gotor-Fernandez, Vicente,de Mattos, Marcos Carlos,de Oliveira, Maria da Conceicao F.,Lemos, Telma L.G.,Gotor, Vicente
experimental part, p. 566 - 570 (2010/08/06)
Whole cells from the Brazilian beans feijao de corda (Vigna unguiculata) have been employed as biocatalysts in different bioreduction processes. Good to excellent selectivities can be obtained in the reduction of aromatic and aliphatic ketones, as well as β-ketoesters, depending on the conversions and the chemoselectivity on the substrate structure. This biocatalyst was also able to reduce the nitro moiety of different aromatic nitro compounds, showing as well enoate reductase activity, and chemoselectively catalyzing the double bond reduction of 4-phenyl-3-buten-2-one with moderate conversion.
Lentinus strigellus: a new versatile stereoselective biocatalyst for the bioreduction of prochiral ketones
Barros-Filho, Bartholomeu A.,de Oliveira, Maria da Conceicao F.,Lemos, Telma L.G.,de Mattos, Marcos C.,Gonzalo, Gonzalo de,Gotor-Fernandez, Vicente,Gotor, Vicente
experimental part, p. 1057 - 1061 (2009/10/02)
Growing cells of the basiodiomycete Lentinus strigellus in potato-dextrose broth have been used for the first time as a biocatalyst in the stereoselective reduction of aromatic and aliphatic ketones. Most of the aromatic ketones were converted into the corresponding optically active alcohols in up to >99% enantiomeric excess under very mild reaction conditions. Among the aliphatic ketones tested, 2-octanone was enzymatically reduced by this microorganism to enantiopure (S)-2-octanol with almost complete conversion.
Enantioselective addition of dimethylzinc to aldehydes catalyzed by N-substituted mandelamide-Ti(IV) complexes
Blay, Gonzalo,Fernandez, Isabel,Hernandez-Olmos, Victor,Marco-Aleixandre, Alicia,Pedro, Jose R.
, p. 1953 - 1958 (2007/10/03)
Amides derived from (S)-(+)-mandelic acid in the presence of titanium isopropoxide catalyze the enantioselective addition of dimethylzinc to aromatic aldehydes with good yields and ee up to 90%.
PHEROMONES AND METHOD OF PREVENTING INFESTATION OF CONTARINIA NASTURTII
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Page/Page column 9, (2008/06/13)
The present invention relates to a pheromone mixture comprising 2,9-diacetoxyundecane, 2,10-diacetoxyundecane and 2-acetoxyundecane, as a racemate or, biologically active stereoisomers thereof, as well as a method for monitoring and/or mating disruption of swede midge, Contarinia nasturtii, in Brassica vegetables, in particular Brussels sprouts, cauliflower and broccoli.
High-efficiency and minimum-waste continuous kinetic resolution of racemic alcohols by using lipase in supercritical carbon dioxide
Matsuda, Tomoko,Watanabe, Kazunori,Harada, Tadao,Nakamura, Kaoru,Arita, Yoshitaka,Misumi, Yukibiro,Ichikawa, Shinichiro,Ikariya, Takao
, p. 2286 - 2287 (2007/10/03)
A novel continuous-flow scCO2 process for kinetic resolution of racemic alcohols can be performed with an immobilized lipase to lead to a quantitative mixture of the corresponding optically active acetates with up to 99% ee and unreacted alcohols with up to 99% ee, in which the productivity of the optically active compounds was improved by over 400 times compared to the corresponding batch reaction using scCO2.
Kinetic resolution of propargylic and allylic alcohols by Candida antarctica lipase (Novozyme 435)
Raminelli, Cristiano,Comasseto, Joao V.,Andrade, Leandro H.,Porto, Andre L.M.
, p. 3117 - 31722 (2007/10/03)
A number of chiral propargylic and allylic alcohols were resolved by lipase-catalyzed kinetic resolution (Novozyme 435). In some cases the enantiomeric excess was high (up to >99%).
Opening of tartrate acetals using dialkylboron bromide: Evidence for stereoselectivity downstream from ring fission
Guindon, Yvan,Ogilvie, William W.,Bordeleau, Josee,Cui, Wei Li,Durkin, Kathy,Gorys, Vida,Juteau, Helene,Lemieux, Rene,Liotta, Dennis,Simoneau, Bruno,Yoakim, Christiane
, p. 428 - 436 (2007/10/03)
Johnson-type acetals derived from dimethyl tartrate give, after opening with Me2BBr and cuprate displacement, secondary alcohols with high diastereoselectivity (>30:1). The mechanism proposed for the induction of diastereoselectivity is downstream from the ring fission. It implies a direct participation of the Lewis acid as a source of nucleophile and the stereospecific transformation of the resulting bromo acetal through an invertive and temperature-dependent process. The acetals are prepared by reaction of the desired aldehyde with dimethyl tartrate. Removal of the auxiliary is accomplished through Sml2 reduction or by an addition - elimination protocol using methoxide.
