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Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols

Xile Hu, Zhikun Zhang

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols whic ...

Wiley-VCH Verlag GmbH2021

Enantioselective Total Synthesis of (+)-Nordasycarpidone, (+)-Dasycarpidone, and (+)-Uleine

Qian Wang, Jieping Zhu, Cédric Fung, Bastien Delayre

The structure of uleine type alkaloids is characterized by the presence of a bridged tetracyclic hexahydro-1H-1,5-methanoazocino[4,3-b]indole ring system 1. Various strategies have been developed to access this polycyclic structural motif. We report herein ...

2021

Electrodes for Paracetamol Sensing Modified with Bismuth Oxide and Oxynitrate Heterostructures: An Experimental and Computational Study

Sandro Carrara, Filippo Franceschini

In this work, novel platforms for paracetamol sensing were developed by the deposition of Bi2O3, Bi5O7NO3 and their heterostructures onto screen-printed carbon-paste electrodes. An easy and scalable solid state synthesis route was employed, and by setting ...

MDPI2021

Catalytic Enantioselective Benzilic Ester Rearrangement

Qian Wang, Jieping Zhu, Hua Wu

We report the first examples of catalytic enantioselective benzilic ester rearrangement reaction. In the presence of a catalytic amount of Cu(OTf)(2) and a chiral box ligand under mild conditions, reaction of 2,3-diketoesters with alcohols afforded structu ...

Wiley-VCH Verlag GmbH2020

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Jérôme Waser, Bastian Antoine Rodolphe Claude Muriel, Vincent Géry C Pirenne

This review describes the development of enantioselective methods for the ring opening of cyclopropanes. Both approaches based on the reaction of nonchiral cyclopropanes and (dynamic) kinetic resolutions and asymmetric transformations of chiral substrates ...

2021

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

Harald Brune, Roland Widmer, Aliaksandr Yakutovich, Jan Prinz, Samuel Thomas Stolz

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

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

Asymmetric Total Synthesis of (-)-Arborisidine and (-)-19-epi-Arborisidine Enabled by a Catalytic Enantioselective Pictet-Spengler Reaction

Qian Wang, Jieping Zhu, Rémi Julien Sylvain Andres

A five-step total synthesis of arborisidine, a caged pentacyclic monoterpene indole alkaloid, has been accomplished in both racemic and enantioselective manners. The synthesis features the following three key steps: (a) a regioselective Pictet-Spengler rea ...

AMER CHEMICAL SOC2020

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, Ugo Jonathan Orcel, Mikus Purins, Phillip Gulliver Dominic Greenwood, Luca Buzzetti

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

Diiron Complexes with a Bridging Functionalized Allylidene Ligand: Synthesis, Structural Aspects, and Cytotoxicity

Paul Joseph Dyson, Lucinda Kate Batchelor, Silvia Schoch

Regio- and stereoselective nucleophilic attack of cyanide (from NBu4CN) to cationic diiron vinyliminium compounds [Fe2Cp2(CO)(mu-CO){mu-eta(1):eta(3)-C-(R')C(R '')-CNMe2}]CF3SO3 ([1a-f]CF3SO3) affords the nitrile-aminoallylidene derivatives 2a-f in good to ...

AMER CHEMICAL SOC2020

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