Vinylepoxides in Organic Synthesis

Olofsson, Berit; Somfai, Peter

doi:10.1002/3527607862.ch9

Cited by 56 publications

(55 citation statements)

References 123 publications

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“…To gain insight with regard to the origin of the Z or E stereoselectivity on the vinyl substituent according to the diazo compound used, DFT calculations 22 were performed ( Figure 2). The initial ruthenium carbene I´ was found to be in conformational equilibrium with two possible isomers arising from the rotation along the Ru=C bond.…”

Section: Scheme 4 Mechanistic Hypothesismentioning

confidence: 99%

[2 + 1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines

et al. 2016

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Aza-alkynals undergo a cyclization reaction with diazo compounds in the presence of catalytic amounts of Cp*RuCl(cod) to afford vinyl epoxypyrrolidines, valuable building blocks for the synthesis of biologically active molecules. Ruthenium vinyl carbene intermediates have been invoked to explain the overall [2+1] cycloaddition (epoxy-annulation reaction). The reaction proceeds under mild conditions and in short reaction times (5-80 min) with complete (Z)or (E)-stereoselectivity on the vinyl substituent depending on the nature of the diazo compound used. Theoretical calculations support a mechanistic rationale to explain this controlled process.

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Section: Scheme 4 Mechanistic Hypothesismentioning

confidence: 99%

[2 + 1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines

et al. 2016

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“…Vinylepoxides comprise an interesting class of electrophiles, as they possess more than one nucleofugal site; therefore, nucleophilic addition can proceed either in an S N 2 or S N 2′ fashion 8. In the case at hand, selective S N 2′ addition is necessary for the subsequent 1,4‐Brook rearrangement.…”

Section: Through‐bond/through‐space Arc With Linchpin 22[a]mentioning

confidence: 99%

A functional high‐content miRNA screen identifies miR‐30 family to boost recombinant protein production in CHO cells

Fischer

Buck

Wagner

et al. 2014

Biotechnology Journal

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The steady improvement of mammalian cell factories for the production of biopharmaceuticals is a key challenge for the biotechnology community. Recently, small regulatory microRNAs (miRNAs) were identified as novel targets for optimizing Chinese hamster ovary (CHO) production cells as they do not add any translational burden to the cell while being capable of regulating entire physiological pathways. The aim of the present study was to elucidate miRNA function in a recombinant CHO-SEAP cell line by means of a genome-wide high-content miRNA screen. This screen revealed that out of the 1, 139 miRNAs examined, 21% of the miRNAs enhanced cell-specific SEAP productivity mainly resulting in elevated volumetric yields, while cell proliferation was accelerated by 5% of the miRNAs. Conversely, cell death was diminished by 13% (apoptosis) or 4% (necrosis) of all transfected miRNAs. Besides these large number of identified target miRNAs, the outcome of our studies suggest that the entire miR-30 family substantially improves bioprocess performance of CHO cells. Stable miR-30 over expressing cells outperformed parental cells by increasing SEAP productivity or maximum cell density of approximately twofold. Our results highlight the application of miRNAs as powerful tools for CHO cell engineering, identified the miR-30 family as a critical component of cell proliferation, and support the notion that miRNAs are powerful determinants of cell viability.

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“…The preparation of vinyl epoxides has also been reviewed recently [333], as have as other topical works mentioned in the appropriate context below.…”

Section: Synthesis Of Oxiranesmentioning

confidence: 99%

Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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Vinylepoxides in Organic Synthesis

Cited by 56 publications

References 123 publications

[2 + 1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines

[2 + 1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines

A functional high‐content miRNA screen identifies miR‐30 family to boost recombinant protein production in CHO cells

Three‐Membered Heterocycles. Structure and Reactivity

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