A Giese reaction for electron-rich alkenes

Huang, Qi; Suravarapu, Sankar Rao; Renaud, Philippe (2021). A Giese reaction for electron-rich alkenes. Chemical Science, 12(6), pp. 2225-2230. The Royal Society of Chemistry 10.1039/d0sc06341j

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A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4-tert-butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very favorable polar effects supporting the chain process and minimizing undesired polar reactions. The stereoselective hydroalkylation of chiral N-(alk-1-en-1-yl)oxazolidin-2-ones takes place with good to excellent diastereocontrol.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Huang, Qi and Renaud, Philippe

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

2041-6520

Publisher:

The Royal Society of Chemistry

Language:

English

Submitter:

Franziska Bornhauser-Rufer

Date Deposited:

24 Jun 2021 11:48

Last Modified:

24 Jun 2021 11:57

Publisher DOI:

10.1039/d0sc06341j

BORIS DOI:

10.48350/157100

URI:

https://boris.unibe.ch/id/eprint/157100

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