Publications related to Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Related publications (27)

Chemodivergent Asymmetric Synthesis via Catalytically Formed Chiral Auxiliary

In summary, the development of the catalytically formed chiral auxiliary concept is described. In this approach, an oxazolidine auxiliary is installed via enantioselective Pd catalysis from readily available starting materials in an enantioselective tether ...

EPFL2023

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Rémi Hugo Lavernhe

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles

Jérôme Waser, Matthew Wodrich, Vu Trung Tin Nguyen

We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...

2023

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

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

Guillaume Dominique Pisella

The development of a sequential copper-catalyzed oxy-alkynylation/intramolecular [4+2] cycloaddition of allenes and arenes was investigated at first. This one-pot protocol allowed the construction of complex polycylic architectures with high efficiency fro ...

EPFL2021

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Bastian Antoine Rodolphe Claude Muriel

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

EPFL2021

Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary

Jérôme Waser, Mikus Purins, Phillip Gulliver Dominic Greenwood, Luca Buzzetti

Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity ...

2020

Palladium-Catalyzed Functionalization of Olefins and Alkynes: From Oxyalkynylation to Tethered Dynamic Kinetic Asymmetric Transformations (DYKAT)

Jérôme Waser, Stefano Nicolai, Bastian Antoine Rodolphe Claude Muriel, Mikus Purins, Ugo Jonathan Orcel, Luca Buzzetti, Phillip Gulliver Dominic Greenwood

This review presents an account of the palladium-catalyzed functionalizations of alkenes and alkynes developed at the Laboratory of Catalysis and Organic Synthesis (LCSO). Starting from the intramolecular oxy- and aminoalkynylation of alkenes, tethered met ...

2020

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations

Daria Grosheva

Asymmetric metal-catalyzed C-H functionalization has enjoyed great success as a powerful strategy for the rapid construction of elaborate structures from simple precursors. For example, aryl (pseudo)halides have been extensively employed as electrophilic s ...

EPFL2019

Chiral N-Heterocyclic Carbene Ligands for Asymmetric Catalysis

Johannes Diesel

N-Heterocyclic carbenes (NHCs) are the ligands of choice in a large variety of transformations entailing different transition metals. However, the number of chiral NHCs suitable as stereocontrolling ligands in asymmetric catalysis remains limited. In parti ...

EPFL2019

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

Stereoselective synthesis of alkenes via base-metal-catalyzed addition reactions to alkynes and activation of hydrogen peroxide and carbon dioxide by iron complexes

Fedor Zhurkin

Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...

EPFL2017

"Divergent Total Synthesis of (-)-Rhazinilam, (-)-Leucomidine B and (+)-Leuconodine F" and "Synthetic Studies Towards Sarpagine-Related Indoles"

Dylan Jean Robert Dagoneau

The work presented in this thesis focuses on the synthesis of monoterpene indole alkaloids. The first part describes the divergent total synthesis of (-)-rhazinilam, (-)-leucomidine B and (+)-leuconodine F, three structurally distinct natural products of t ...

EPFL2017

Access to Chiral Cyclopentane Scaffolds by Enantioselective Nickel-Catalyzed Annulations

Joachim Sven Ernst Ahlin

The cyclopentane scaffold has attracted much attention due to its ubiquity in numerous bioactive natural products such as prostaglandins and polyquinanes. However, despite a plethora of available procedures to access this motif, a lack of methods that riva ...

EPFL2016

Racemization of undesired enantiomers: Immobilization of mandelate racemase and application in a fixed bed reactor

Production of optically pure products can be based on simple unselective synthesis of racemic mixtures combined with a subsequent separation of the enantiomers; however, this approach suffers from a 50% yield limitation which can be overcome by racemizatio ...

Wiley-V C H Verlag Gmbh2016

Enantioselective Synthesis of Putative Lipiarmycin Aglycon Related to Fidaxomicin/Tiacumicin B

Jieping Zhu

An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1) Brown’s enantioselective alkoxyallylboration and allylation of aldehydes, 2) chain elongation by iterative Horner–Wadsworth– Emmons olefination, 3) Evans aldo ...

Wiley-Blackwell2015

Chiral Cyclopentadienyls: Enabling Ligands for Asymmetric Rh(III)-Catalyzed C-H Functionalizations

Nicolai Cramer, Baihua Ye

Transition-metal catalyzed C-H functionalizations became a complementary and efficient bond-forming strategy over the past decade. In this respect, Cp*Rh(III) complexes have emerged as powerful catalysts for a broad spectrum of reactions giving access to s ...

American Chemical Society2015

Chiral Cyclopentadienyl Rh(III)-Complexes for Asymmetric C-H Functionalizations

Baihua Ye

Pentamethylcyclopentadienyl (Cp*) based transition-metal-catalyzed C-H functionalization has become an important synthetic tool for the construction of molecular complexity from simple starting materials. Despite their high potential, the corresponding asy ...

EPFL2015

Diaminophosphine Oxide Ligand Enabled Asymmetric Nickel-Catalyzed Hydrocarbamoylations of Alkenes

Nicolai Cramer, Pavel Alexandrovich Donets

Chiral trivalent phosphorus species are the dominant class of ligands and the key controlling element in asymmetric homogeneous transition-metal catalysis. Here, novel chiral diaminophosphine oxide ligands are described. The arising catalyst system with ni ...

Amer Chemical Soc2013