Publication

Catalytic Enantioselective Pinacol and Meinwald Rearrangements for the Construction of Quaternary Stereocenters

Qian Wang, Jieping Zhu, Hua Wu
2019
Journal Articles

Abstract

The development of enantioselective pinacol rearrangement is extremely challenging due to the likelihood involvement of the carbenium intermediate that renders the stereochemical communication between catalyst and substrate difficult to achieve. Herein, we report chiral N-triflyl phosphoramide-catalyzed enantioselective pinacol rearrangement of 1,2-tertiary diols and mechanistically related Meinwald rearrangement of tetrasubstituted epoxides for the synthesis of enantioenriched 2-alkynyl-2-arylcyclohexanones and 2,2-diarylcyclohexanones, respectively. Total synthesis of (+)-mesembrane featuring the catalytic enantioselective pinacol rearrangement as a key strategic step is also documented.

Official source

https://infoscience.epfl.ch/entities/publication/3f1e48f2-8c18-4a6f-9e19-089a1b2c6f3e

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Qian Wang, Jieping Zhu, Hua Wu
2019
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3f1e48f2-8c18-4a6f-9e19-089a1b2c6f3e

About this result

Related concepts (11)

Total synthesis

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest.

Chemical synthesis

In chemistry, chemical synthesis (chemical combination) is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In modern laboratory uses, the process is reproducible and reliable. A chemical synthesis involves one or more compounds (known as reagents or reactants) that will experience a transformation when subjected to certain conditions. Various reaction types can be applied to formulate a desired product.

Likelihood function

In statistical inference, the likelihood function quantifies the plausibility of parameter values characterizing a statistical model in light of observed data. Its most typical usage is to compare possible parameter values (under a fixed set of observations and a particular model), where higher values of likelihood are preferred because they correspond to more probable parameter values.

Related publications (1)

Catalytic Enantioselective Pinacol and Meinwald Rearrangements for the Construction of Quaternary Stereocenters

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Nouvelles approches synthétiques de prodrogues de cyclosporine A et d'analogues antiviraux