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Publication

An Enantioselective Cp x Rh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

Nicolai Cramer, Shouguo Wang
2019
Journal Articles

Abstract

A chiral CpxRhIII catalyst system in situ generated from a CpxRhI(cod) precatalyst and bis(o‐toluoyl) peroxide as activating oxidant was developed for a C−H activation/ring‐opening sequence between aryl ketoxime ethers and 2,3‐diazabicyclo[2.2.1]hept‐5‐enes. This transformation provides access to densely functionalized chiral cyclopentenylamines in excellent yields and enantioselectivities of up to 97:3 er. The reported method is also well suitable for asymmetric alkenyl C−H functionalizations of α,β‐unsaturated oxime ethers, furnishing skipped dienes with high levels of enantiocontrol.

Official source

https://infoscience.epfl.ch/entities/publication/3ff7514e-2a91-4aec-90fc-d5a6d12b97fd

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Nicolai Cramer, Shouguo Wang
2019
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3ff7514e-2a91-4aec-90fc-d5a6d12b97fd

About this result

Related concepts (6)

Oxime

In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides () with general structure . Oximes are usually generated by the reaction of hydroxylamine with aldehydes () or ketones (). The term oxime dates back to the 19th century, a combination of the words oxygen and imine.

Lithium aluminium hydride

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage. LAH is a colourless solid but commercial samples are usually gray due to contamination.

Aldehyde

In organic chemistry, an aldehyde (ˈældᵻhaɪd) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen.

Related publications (1)

An Enantioselective Cp x Rh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

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Nickel-catalyzed Hydrosilylation of Alkenes and Transition-Metal-Free Intermolecular α-C-H Amination of Ethers