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Concept

Enantiomeric excess

Related publications (18)

Near-Enantiopure Trimerization of 9-Ethynylphenanthrene on a Chiral Metal Surface

Harald Brune, Samuel Thomas Stolz, Aliaksandr Yakutovich

Enantioselectivity in heterogeneous catalysis strongly depends on the chirality transfer between catalyst surface and all reactants, intermediates, and the product along the reaction pathway. Herein we report the first enantioselective on-surface synthesis ...

Wiley-VCH Verlag GmbH2020

Exploiting the chirality of intermetallic PdGa

Samuel Thomas Stolz

The intermetallic compound PdGa has recently attracted considerable interest for combining high catalytic activity with high reaction selectivity in symmetric heterogeneous catalysis, in particular semi-hydrogenation of acetylene and methanol steam reformi ...

EPFL2020

Iridium-catalyzed acid-assisted asymmetric hydrogenation of oximes to hydroxylamines

Nicolai Cramer, Josep Más-Roselló

Asymmetric hydrogenations are among the most practical methods for the synthesis of chiral building blocks at industrial scale. The selective reduction of an oxime to the corresponding chiral hydroxylamine derivative remains a challenging variant because o ...

American Association for the Advancement of Science2020

Chiral Cyclopentadienyl Ligands: Design, Syntheses, and Applications in Asymmetric Catalysis

Nicolai Cramer, Benoît Daniel Bertrand Audic, Josep Más-Roselló, Aragorn Nathan Laverny, Ana Garcia Herraiz

The creation of new chiral ligands capable of providing high stereocontrol in metal-catalyzed reactions is crucial in modern organic synthesis. The production of bioactive molecules as single enantiomers is increasingly required, and asymmetric catalysis w ...

Wiley-VCH Verlag GmbH2021

Catalytic Enantioselective Transformations with Chiral Cyclopentadienyl Ruthenium(II) Complexes

Sung Hwan Park

The chemistry of cyclopentadienyl ruthenium(II) complexes plays an important role in ruthenium catalysis because of its high potential for various transformations. However, asymmetric catalysis with chiral cyclopentadienyl ruthenium(II) complexes is still ...

EPFL2020

Development of Catalytic Asymmetric C-H Functionalizations with Chiral Cyclopentadienyl Iridium(III) Complexes

Yun-Suk Jang

Cp*Ir(III) catalyzed C-H functionalization is a growing field, since it provides novel complementary reactivities, but enantioselective C-H functionalization reactions with this metal remain a niche. This thesis investigates CpXIr(III) catalyzed asymmetric ...

EPFL2019

Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene

Magalí Alejandra Lingenfelder

A convergent synthesis of racemic 5-amino[6]hexahelicene is described. Cross-coupling reactions are used to assemble a pentacyclic framework, and a metal-catalyzed ring-closure comprises the final step. The enantiomers were separated by means of chromatogr ...

Wiley-Blackwell2016

Phosphoric Acid Catalyzed Diastereo- and Enantioselective Synthesis of Substituted 1,3-Diaminotetralins

Jieping Zhu

The reaction of anilines and phenylacetaldehydes in the presence of chiral phosphoric acid afforded optically active 1,2-trans, 2,3-cis 1,3-diaminotetralins in high yields with excellent diastereo- and enantioselectivities. The trans/cis product was readil ...

Amer Chemical Soc2014

Ruthenium(II) arene PTA (RAPTA) complexes: impact of enantiomerically pure arene ligands

Paul Joseph Dyson, Catherine Marie Amélie Clavel, Kelly Joan Kilpin

Organometallic ruthenium(II) arene complexes containing the PTA ligand ([Ru(eta(6)-arene)Cl-2(PTA)], PTA = 1,3,5-triaza-7-phosphatricyclo-[3.3.1.1] decane, termed RAPTA) show pharmacologically relevant antitumour properties in vitro. Two new enantiomeric p ...

Royal Society of Chemistry2013

Lack of Enantioselectivity in the SULT1A3-catalyzed Sulfoconjugation of Normetanephrine Enantiomers: An In Vitro and Computational Study

Sandrine Gerber, Jean-Baptiste Gualtierotti

(1R)-Normetanephrine is the natural stereoisomeric substrate for sulfotransferase 1A3 (SULT1A3)-catalyzed sulfonation. Nothing appears known on the enantioselectivity of the reaction despite its potential significance in the metabolism of adrenergic amines ...

Wiley-Blackwell2013

Cinchona Alkaloid-Amides Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Enantioselective Synthesis of 2,4-Substituted Azetidines

Jieping Zhu

Mix and go. The quinidine-amide (1)-catalyzed [2+2] cycloaddition between N-sulfonylimines (2) and alkyl 2,3-butadienoate (3) afforded the (R)-azetidines 4 in excellent yields and enantioselectivities. The (S)-enantiomer was obtained when a quinine-amide c ...

Wiley-Blackwell2011

Chiral recognition and supramolecular self-assembly of adsorbed amino acids and dipeptides at the submolecular level

Magalí Alejandra Lingenfelder

This thesis deals with the supramolecular organization of chiral aminoacids and dipeptides on metal surfaces. The emergence of homochirality in biomolecular systems is one of the most intriguing open questions of Nature. The self-assembly and amplification ...

EPFL2008

Embedding an Allylmetal Dimer in a Chiral Cavity: The Unprecedented Stereoselectivity of a Twofold Wittig [1,2]-Rearrangement

Frédéric Bailly

After alpha,alpha'-dimetalation, both 2,2'-diallyloxy-1,1'-binaphthyl and 2,2'-di-2-methylallyloxy-1,1'-binaphthyl undergo the Wittig rearrangement with perfect diastereoselectivity. When racemic 1,1'-binaphthyl-2,2'-diol ("BINOL") is used as the starting ...

2006

Enantiopure helical (supra)molecular arrays containing lanthanides : design, synthesis and properties

Marco Antonio Lama

The diastereoselective synthesis of chiral coordination compounds with d metals proved the effectiveness of the pinene-bipyridine approach in predetermining the chirality at the metal centre. The strong Lewis acidic character of lanthanide cations required ...

EPFL2006

Expeditious asymmetric synthesis of a stereoheptad corresponding to the C(19)-C(27)-ansa chain of rifamycins: Formal total synthesis of Rifamycin S

Pierre Vogel, Maris Turks, Xiaogen Huang

In the presence of sulfur dioxide and an acid promoter, (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenyleth- oxy)penta-1,3-dien-3-yl isobutyrate reacts with (Z)-3-(trimethylsilyloxy)-pent-2-ene giving a silyl sulfinate intermediate that undergoes, in the presence of ...

2005

Enantioselective transformation of α-hexachlorocyclohexane by the dehydrochlorinases LinA1 and LinA2 from the soil bacterium Sphingomonas paucimobilis B90A

Christof Holliger

Sphingomonas paucimobilis B90A contains two variants, LinA1 and LinA2, of a dehydrochlorinase that catalyzes the first and second steps in the metabolism of hexachlorocyclohexanes (R. Kumari, S. Subudhi, M. Suar, G. Dhingra, V. Raina, C. Dogra, S. Lal, J. ...

2005

Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are beta-glucosidase inhibitors

Pierre Vogel

The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAC)(3). The N-subst ...

2005

New developments on silyl 2-alkenyl sulfinates and their applications to the asymmetric synthesis of polypropionate fragments

Xiaogen Huang

Sulphur dioxide reacts with 1-oxydienes generating zwitterions which are quenched by enoxysilanes to form substituted silyl alkenylsulfinates. These intermediates are desilylated with Bu4NF and the resulting sulfinates react with MeI giving the correspondi ...

EPFL2004