Simona Hybelbauerová

Charles University

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Martin Kotora

Charles University

Ján Veselý

Charles University

Ivana Cı́sařová

Charles University

Martin Kamlar

Charles University

ŠJ

Štěpánka Janková

Charles University

Jindřich Jindřich

Charles University

Jana Roithová

Radboud University Nijmegen

PŠ

Petr Štěpnička

Charles University

Martin Dračínský

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Jan Sejbal

Charles University

Cooperative Institutions

Charles University

Czech Academy of Sciences

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Universitat de Barcelona

Centre National de la Recherche Scientifique

University of Chemistry and Technology, Prague

University of Pardubice

University of Southampton

General University Hospital in Prague

Czech Academy of Sciences, Institute of Macromolecular Chemistry

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First Enantioselective Organocatalytic Addition of Nitromethylphenylsulfone to Enals. Enantioselective Synthesis of Cyclohexenones Bearing 3 Contiguousstereogeniccenters

Current Organic Synthesis (2013)

Ramón Rios Simona Hybelbauerová Ivana Csarova Ján Veselý

A highly enantioselectiveorganocatalyticnitromethylphenylsulfone addition to aliphatic α,β-unsaturated aldehydes is reported. The reaction is catalyzed by simple and commercially available secondary amines, affording the cyclic compounds in moderate yields, good diastereoselectivities and excellent enantioselectivities. Keywords: Cascade reaction, enantioselective, organocatalysis, asymmetric synthesis, secondary amine, cyclization.

10.2174/1570179411310030008

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Synthesis of 1,2,3,4‐Tetramethyl‐ and 1,2,3,4‐Tetraethylfluorene through a Dewar Benzene Pathway

European Journal of Organic Chemistry (2012)

Štěpánka Janková Jiří Schulz Simona Hybelbauerová Ivana Cı́sařová Petr Štěpnička

Abstract A simple and selective synthesis of 1,2,3,4‐tetra(m)ethylfluorenones and ‐fluorenes was achieved by using Dewar benzenes as important intermediates. The corresponding Dewar benzenes were prepared by reactions of tetraalkylcyclobutadiene–AlCl 3 complexes with methyl phenylpropynoate. Their subsequent hydrolysis followed by photochemical rearrangement provided substituted biphenylcarboxylic acids. Treatment of the prepared acids with thionyl chloride gave rise to the fluorenones, which were reduced to the respective fluorenes. A Ru complex with 1,2,3,4‐tetraethylfluorenone was prepared.

Thionyl chloride

Benzene derivatives

10.1002/ejoc.201201343

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Citations (6)

CCDC 873451: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

Štěpánka Janková Joachim Schulz Simona Hybelbauerová Ivana Cı́sařová Petr Štěpnička

10.5517/ccy9wvy

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ChemInform Abstract: Organocatalytic Enantioselective Allylic Alkylation of MBH Carbonates with β‐Keto Esters.

ChemInform (2014)

Martin Kamlar Simona Hybelbauerová Ivana Cı́sařová Ján Veselý

Tsuji–Trost reaction

10.1002/chin.201451091

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Experimenty s přírodními látkami v chemickém vzdělávání na SŠ – názory středoškolských učitelů

Scientia in educatione (2019)

Michala Opatová Simona Hybelbauerová

Tento článek přináší názory středoškolských učitelů chemie na téma experimenty s přírodními látkami v chemickém vzdělávání. Prostřednictvím interaktivního dotazníku učitelé odpovídali na otázky k teoretické i experimentální výuce tohoto tématu. Cílem výzkumu bylo zjistit, jaké experimenty s přírodními látkami učitelé zařazují do výuky, jestli rozšiřují téma i do jiných oblastí, než jak je uváděno v rámcových vzdělávacích programech, a kde nacházejí ke zmíněným experimentům inspiraci. Výsledky výzkumu poslouží mj. ke zpracování sbírky s návody na inovované či méně známé experimenty s přírodními látkami.

10.14712/18047106.71

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Unusual p‐Coumarates from the Stems of Vaccinium myrtillus

Helvetica Chimica Acta (2009)

Simona Hybelbauerová Jan Sejbal Martin Dračínský Iva Rudovská Bohumı́r Koutek

Abstract The two previously unreported esters 1 and 2 of pentane‐2,4‐diol and p ‐coumaric acid (=3‐(4‐hydroxyphenyl)prop‐2‐enoic acid) along with 13 known compounds including 6 oleanane‐ and ursane‐type triterpenoids were isolated from MeOH extracts of the stems of Vaccinium myrtillus. The structures of the new compounds were assigned as (2 S ,4 R )‐4‐( β ‐ D ‐glucopyranosyloxy)pentan‐2‐yl (2 E )‐ p ‐coumarate ( 1 ) and its aglycone 2 on the basis of 1D‐ and 2D‐NMR spectroscopic analyses of the isolated and synthesized compounds and molecular modelling experiments. This is the first report on the occurrence of a chiral pentane‐2,4‐diol linker between the phenol‐derived acid and a glycoside part in natural products.

Vaccinium myrtillus

Aglycone

Oleanane

Terpene

Pentane

10.1002/hlca.200900220

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Citations (7)

Highly Enantioselective Addition of 1‐Fluoro‐1‐nitro(phenylsulfonyl)methane to α,β‐Unsaturated Aldehydes

European Journal of Organic Chemistry (2010)

Martin Kamlar Natalia Bravo Andrea‐Nekane R. Alba Simona Hybelbauerová Ivana Cı́sařová

Abstract An organocatalytic, highly enantioselective addition of 1‐fluoro‐1‐nitro(phenylsulfonyl)methane to α,β‐unsaturated aldehydes is reported. The reaction is simply catalyzed by secondary amines and furnishes the corresponding fluorinated derivatives in good yields, with moderate diastereoselectivities and excellent enantioselectivities. The absolute configuration of the major diastereomers was unambiguously ascertained by X‐ray diffraction analysis.

Diastereomer

Absolute Configuration

10.1002/ejoc.201000851

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Citations (29)

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

Beilstein Journal of Organic Chemistry (2017)

M Blahová Sergey K. Filippov Ľubomír Kováčik Jiřı́ Horský Simona Hybelbauerová

Monosubstituted derivatives of γ-cyclodextrin (γ-CD) are suitable building blocks for supramolecular polymers, and can also serve as precursors for the synthesis of other regioselectively monosubstituted γ-CD derivatives. We prepared a set of monosubstituted 2I-O-, 3I-O-, and 6I-O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of γ-CD using two different methods. A key step of the first synthetic procedure is a cross-metathesis between previously described regioisomers of mono-O-allyl derivatives of γ-CD and 2-vinylnaphthalene which gives yields of about 16-25% (2-5% starting from γ-CD). To increase the overall yields, we have developed another method, based on a direct alkylation of γ-CD with 3-(naphthalen-2-yl)allyl chloride as the alkylating reagent. Highly regioselective reaction conditions, which differ for each regioisomer in a used base, gave the monosubstituted isomers in yields between 12-19%. Supramolecular properties of these derivatives were studied by DLS, ITC, NMR, and Cryo-TEM.

Structural isomer

10.3762/bjoc.13.248

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Preparation and Conformational Study of B-Ring Substituted Lupane Derivatives

Collection of Czechoslovak Chemical Communications (2006)

Martin Dračínský Simona Hybelbauerová Jan Sejbal Miloš Buděšı́nský

New lupane-type triterpenoids with 5(6) double bond were prepared using the method of partial demethylation on carbon C-4. Hydroboration of the double bond led to 6α-hydroxy derivative. By the oxidation and following reduction of 6α-hydroxy derivative the 6-oxo and 6β-hydroxy derivatives were prepared. A new method for selective oxidation of secondary hydroxy group in the presence of primary hydroxy group was performed. The conformation of ring A of new lupane-type 3-oxo derivatives with a substituent on ring B was elucidated on the bases of 1 H and 13 C NMR spectra and molecular modelling.

Hydroboration

Derivative (finance)

Triple bond

Demethylation

10.1135/cccc20061131

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Citations (6)

Synthesis of 3I-O and 2I-O-monosubstituted derivatives of per-6-azido-β-cyclodextrin—potential molecular scaffolds

Carbohydrate Research (2012)

Martin Popr Simona Hybelbauerová Jindřich Jindřich

Propargyl bromide

Structural isomer

Allyl bromide

Propargyl

10.1016/j.carres.2012.09.003

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Citations (1)