A chemoenzymatic route to chiral siloxanes

Naoum, Ravi; Séguin, Jacqueline P.; Trant, John F.; Frampton, Mark B.; Hudlický, Tomáš; Zelisko, Paul M.

doi:10.1016/j.tet.2016.05.032

Cited by 3 publications

(3 citation statements)

References 25 publications

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“…For example, chiral diols and siloxane were coupled (66% yield) using dioxygenase and N435 (Lipozyme RM-IM and Lipozyme TL-IM were not active in this reaction). 311 3.1.2. Production of optically pure products.…”

Section: Lewatit Vp Oc 1600mentioning

confidence: 99%

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Ortíz

Ferreira

Barbosa

et al. 2019

Catal. Sci. Technol.

454

360

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Section: Lewatit Vp Oc 1600mentioning

confidence: 99%

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Ortíz

Ferreira

Barbosa

et al. 2019

Catal. Sci. Technol.

454

360

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“…, As shown in Scheme , four types of CM products (expressed as CM1, CM2, CM3, and CM4) as well as SM products can be considered in the reaction. 1 H- and 13 C NMR spectra of the CM products ,− are shown in Figures S17–S26 in the Supporting Information (SI)…”

Section: Resultsmentioning

confidence: 99%

Efficient Conversion of Renewable Unsaturated Fatty Acid Methyl Esters by Cross-Metathesis with Eugenol

Samart

Tsutsumi

et al. 2018

ACS Omega

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Cross-metathesis of unsaturated fatty acid methyl esters (methyl oleate (MO), methyl petroselinate (MP), and methyl erucate (ME), obtained from vegetable oils) with eugenol (obtained from clove oil) proceeded under green, mild conditions (in 2-propanol or ethanol at 50 °C) in the presence of a ruthenium-carbene catalyst (called a second-generation Grubbs catalyst). These metathesis reactions proceeded with both high conversion (>90% of MO, MP) and selectivity (>98%) even with low catalyst loading (0.1 mol % Ru).

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“…When faced with two seemingly equivalent hydroxyl groups, Zelisko et al. showed that the lipase preferentially reacted with the less sterically encumbered hydroxyl group located distally to an acetonide motif; this reinforced the theme that, although CalB is known to be rather promiscuous, as far as substrate selection goes, there are some limitations to this accepted behavior …”

Section: Accessing Unique Structures By Using Lipasementioning

confidence: 99%

Biocatalysis in Silicon Chemistry

Frampton

Zelisko

2017

Chemistry An Asian Journal

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The application of biocatalytic or chemoenzymatic techniquesi ns ilicon chemistry serves two roles:i tp rovides ag reater understanding of the processing of silicon species by natural systems, such as plants, diatoms, and sponges, as well openingu pa venues to green methodologies in the field. In the latter case, biocatalytic approaches have been applied to the synthesis of small-molecule systems and polymeric materials. Often these biocatalytic approaches allow access to molecular structures under mild conditions and, in some cases, molecular structures that are not accessible throught raditional chemical methodologies. Ar eview of recent advances in the applications of biocatalysis in silicon chemistry is presented.

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A chemoenzymatic route to chiral siloxanes

Cited by 3 publications

References 25 publications

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Efficient Conversion of Renewable Unsaturated Fatty Acid Methyl Esters by Cross-Metathesis with Eugenol

Biocatalysis in Silicon Chemistry

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