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Concept

Stereocenter

Related publications (28)

Catalytic Enantioselective Synthesis of Inherently Chiral Macrocycles by Dynamic Kinetic Resolution

Jieping Zhu, Shuo Tong

Kinetically fast racemization of chiral substrates through an achiral intermediate and enantioselective functionalization of one of the enantiomeric substrates forms the basis of the dynamic kinetic resolution (DKR) of centrally chiral molecules. We report ...

2024

Chalcogen bonding catalysis

Jieping Zhu

Catalysts play a major role in chemical synthesis, and catalysis is considered to be a green and economic process. Catalysis is dominated by covalent interactions between the catalyst and substrate. The design of non-covalent catalysts came into limelight ...

Royal Society of Chemistry2024

Enantioselective Total Synthesis of (+)-Stephadiamine

Qian Wang, Jieping Zhu, Guang Li, Baochao Yang

An asymmetric synthesis of (+)-stephadiamine has been accomplished featuring (a) an enantioselective dearomatizative Michael addition to generate a quaternary stereocenter; (b) a domino sequence involving reductive generation of nitrone from γ-nitro ketone ...

2023

Chiral magnetohydrodynamics with zero total chirality

Salim Bennouna

We study the evolution of magnetic fields coupled with chiral fermion asymmetry in the framework of chiral magnetohydrodynamics with zero initial total chirality. The initial magnetic field has a turbulent spectrum peaking at a certain characteristic scale ...

American Physical Society2023

Dielectric Tetramer Nanoresonators Supporting Strong Superchiral Fields for Vibrational Circular Dichroism Spectroscopy

Hatice Altug, Yasaman Jahani, Felix Ulrich Brikh, Ming-Lun Tseng, Longfang Ye

Chirality (C) is a fundamental property of objects, in terms of symmetry. It is extremely important to sense and distinguish chiral molecules in the fields of biochemistry, science, and medicine. Vibrational circular dichroism (VCD) spectroscopy, obtained ...

Amer Chemical Soc2023

Enantio- and diastereoselective construction of vicinal C(sp(3)) centres via nickel-catalysed hydroalkylation of alkenes

Xile Hu, Srikrishna Bera, Chao Fan

In drug discovery, the proportion of aliphatic carbons (C(sp(3))) and the presence of chiral carbons in organic molecules are positively correlated to their chance of clinical success. Although methods exist for the synthesis of chiral C(sp(3))-rich molecu ...

2022

Intermolecular Palladium(0)-Catalyzed Atropo-enantioselective C-H Arylation of Heteroarenes

Nicolai Cramer, Qui-Hien Nguyen

Atropisomeric (hetero)biaryls are motifs with increasing significance in ligands, natural products, and biologically active molecules. The straightforward construction of the stereogenic axis by efficient C-H functionalization methods is extremely rare and ...

2020

Correlation between Optical Activity and the Helical Molecular Orbitals of Allene and Cumulenes

Anne-Clémence Corminboeuf, Marc Hamilton Folkmann Garner

Helical frontier molecular orbitals (MOs) appear in disubstituted allenes and even-n cumulenes. Chiral molecules are optically active, but while these molecules are single-handed chiral, p-orbitals of both helicities are present. Here we computationally ex ...

AMER CHEMICAL SOC2020

Construction of Phosphorus and Sulfur Stereogenic Centers by Chiral Cyclopentadienyl Rhodium(III) Catalysis

Yang Sun

Phosphorus- and sulfur-stereogenic compounds are widely used as ligands in asymmetric transition-metal catalysis and as organocatalysts. These molecules also show a large potential for pharmaceutical and agricultural use. However, synthesizing them in a st ...

EPFL2019

Construction of Quaternary Stereocenters by Palladium-Catalyzed Carbopalladation-Initiated Cascade Reactions

Jieping Zhu, Wangqing Kong

The enantioselective synthesis of molecules containing quaternary stereocenters is a field of intense research interest and development. Among the known organic transformations, carbopalladation-initiated domino transformations constitutes a general method ...

Wiley-VCH Verlag GmbH2019

Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting (CpRhIII)-Rh-X-Catalyzed C-H Functionalization

Nicolai Cramer, Marcus Brauns

Chiral sulfoximines with stereogenic sulfur atoms are promising motifs in drug discovery. We report an efficient method to access chiral sulfoximines through a C-H functionalization based kinetic resolution. A rhodium(III) complex equipped with a chiral Cp ...

Wiley-VCH Verlag GmbH2019

Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization

Nicolai Cramer, Johannes Diesel

C-H functionalization has been established as an efficient way to generate molecular complexity. The formation of stereogenic carbon atoms by asymmetric C-H functionalization has seen tremendous progress over the past decade. More recently, the direct cata ...

2019

X-ray Raman optical activity of chiral molecules

Jérémy Raymond Jean Maurice Rouxel

Resonant and off-resonant Raman Optical Activity signals in the X-ray regime (XROA) are predicted. XROA is a chiral-sensitive variant of the spontaneous Resonant Inelastic Scattering (RIXS) signal. Thanks to the highly localized nature of core excitations, ...

2019

Asymmetric Alkenyl C−H Functionalization by Cp x Rh III forms 2 H ‐Pyrrol‐2‐ones through [4+1]‐Annulation of Acryl Amides and Allenes

Nicolai Cramer, Shouguo Wang

An efficient CpxRhIII‐catalyzed enantioselective alkenyl C−H functionalization/[4+1] annulation of acryl amides and allenes is reported. The described transformation provides straightforward access to enantioenriched α,β‐unsaturated‐γ‐lactams bearing a qua ...

Wiley-VCH Verlag GmbH2019

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 of bicyclo[3.1.0]hexanes by (3+2) annulation of cyclopropenes with aminocyclopropanes

Jérôme Waser, Bastian Antoine Rodolphe Claude Muriel, Alec Gagnebin

We report the convergent synthesis of bicyclo[3.1.0]hexanes possessing an all-carbon quaternary center via a (3 + 2) annulation of cyclopropenes with cyclopropylanilines. Using an organic or an iridium photoredox catalyst and blue LED irradiation, good yie ...

2019

Enantioselective Synthesis of Chiral-at-Sulfur 1,2-Benzothiazines by (CpRhIII)-Rh-x-Catalyzed C-H Functionalization of Sulfoximines

Nicolai Cramer, Yang Sun

Sulfoximines with stereogenic sulfur atoms are attractive structural motifs in drug discovery. A direct catalytic enantioselective method for the synthesis of sulfur-chiral 1,2-benzothiazines from readily accessible diaryl sulfoximines is presented. Rhodiu ...

Wiley-VCH Verlag GmbH2018

Enantioselective Access to 1H-Isoindoles with Quaternary Stereogenic Centers by Palladium(0)-Catalyzed C-H Functionalization

Nicolai Cramer, Daria Grosheva

A catalytic enantioselective method for the synthesis of chiral 1H-isoindoles bearing quaternary stereogenic centers is reported. Powered by readily accessible phosphordiamidite ligands, the presented palladium(0)-catalyzed C-H function-alization uses trif ...

Wiley-VCH Verlag GmbH2018

Rhodium(III)-Catalyzed Enantiotopic C-HActivation Enables Access to P-Chiral Cyclic Phosphinamides

Nicolai Cramer, Yang Sun

Compounds with stereogenic phosphorus atoms are frequently used as ligands for transition-metal as well as organocatalysts. A direct catalytic enantioselective method for the synthesis of P-chiral compounds from easily accessible diaryl phosphinamides is p ...

Wiley-Blackwell2017

Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification

Thomas Rizzo, Michael Zachary Kamrath, Chiara Masellis

The structural characterization of glycans by mass spectrometry is particularly challenging. This is because of the high degree of isomerism in which glycans of the same mass can differ in their stereochemistry, attachment points, and degree of branching. ...

2017