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Catalytic Enantioselective Synthesis of Morpholinones Enabled by Aza-Benzilic Ester Rearrangement

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Recent advances in Rh(I)-catalyzed enantioselective C-H functionalization

Yi Zhang, Nicolai Cramer, Shouguo Wang, Zhen Chen

Chiral carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds are pervasive and very essential in natural products, bioactive molecules, and functional materials, and their catalytic construction has emerged as one of the hottest research fields in syntheti ...

Cambridge2024

Asymmetric Construction of alpha,alpha-Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Jieping Zhu, Hua Wu, Yuping He

An unprecedent asymmetric catalytic benzilic amide rearrangement for the synthesis of a,a-disubstituted piperazinones is reported. The reaction proceeds via a domino [4+1] imidazolidination/formal 1,2-nitrogen shift/1,2-aryl or alkyl migration sequence, em ...

WILEY-V C H VERLAG GMBH2023

TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent

Dina Boyarskaya

Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...

EPFL2023

Go to the Board: A Journey through the Life of Professor David A. Evans

Yimon Aye

By taking a journey through the events that happened during Professor David A. Evans' lifetime in the context of chemical synthesis and drug discovery, this in-focus article reflects upon Professor Evans' lifelong scientific and padegogical impacts on the ...

AMER CHEMICAL SOC2022

Modular Synthesis of Benzocyclobutenes via Pd(II)-Catalyzed Oxidative [2+2] Annulation of Arylboronic Acids with Alkenes

Qian Wang, Jieping Zhu, Takuji Fujii, Simone Gallarati

Benzocyclobutenes (BCBs) are highly valuable compounds in organic synthesis, medicinal chemistry, and materials science. However, catalytic modular synthesis of functionalized BCBs from easily accessible starting materials remains limited. We report herein ...

2022

The development of a titanium(III)-mediated cascade electrocyclisation/rearrangement for theenantioselective total synthesis of indole alkaloids (+)-condyfoline and (-)-tubifoline serve as the basisof the first chapter of this thesis. An introduction will ...

EPFL2022

Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step

Qian Wang, Jieping Zhu, Bastien Delayre

The art of natural product total synthesis is closely associated with two major determinants: the development/application of novel chemical reactions and the innovation in strategic use of classic organic reactions. While purposely seeking/applying a new s ...

2021

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-V C H VERLAG GMBH2021

Enantioselective Total Synthesis of (+)-Alstilobanine C, (+)-Undulifoline, and (-)-Alpneumine H

Qian Wang, Jieping Zhu, Cyril Piemontesi, Guang Li, Nicolas David Gaeng

We report herein the enantioselective total synthesis of three monoterpene indole alkaloids, namely, (+)-alstilobanine C, (+)-undulifoline, and (-)-alpneumine H. The key features of our synthesis include: a) introduction of chirality via enantioselective d ...

WILEY-V C H VERLAG GMBH2021

The development of new catalytic methods for organic synthesis is a critical endeavour in order to obviate the economic and ecological drawbacks of stoichiometric organic synthesis. While catalysis can offer significant advantages in terms of atom-economy, ...

EPFL2021