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) |
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Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Huang, Qi, 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: |
05 Dec 2022 15:51 |
Publisher DOI: |
10.1039/d0sc06341j |
BORIS DOI: |
10.48350/157100 |
URI: |
https://boris.unibe.ch/id/eprint/157100 |
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