Journal
CHEMICAL SCIENCE
Volume 12, Issue 16, Pages 5892-5897Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc00760b
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Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIT) [NRF-2021R1C1C1004605]
- National Research Foundation [NRF-2019R1A6A3A13096586]
- Korea Basic Science Institute (National Research Facilities and Equipment Center) - Ministry of Education [NRF-2020R1A6C101B194]
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An electrochemically driven strategy has been developed for the stereoselective synthesis of protected syn-1,2-diols from vinylarenes using N,N-dimethylformamide (DMF). This approach eliminates the need for transition metal catalysts or external oxidizing agents, providing a simple and efficient route to a variety of protected syn-1,2-diols in a single step. The reaction proceeds through electrooxidation of olefin, followed by a nucleophilic attack of DMF, ultimately resulting in a predominantly syn-diastereoselective product.
We have developed an electrochemically driven strategy for the stereoselective synthesis of protected syn-1,2-diols from vinylarenes with N,N-dimethylformamide (DMF). The newly developed system obviates the need for transition metal catalysts or external oxidizing agents, thus providing an operationally simple and efficient route to an array of protected syn-1,2-diols in a single step. This reaction proceeds via an electrooxidation of olefin, followed by a nucleophilic attack of DMF. Subsequent oxidation and nucleophilic capture of the generated carbocation with a trifluoroacetate ion is proposed, which gives rise predominantly to a syn-diastereoselectivity upon the second nucleophilic attack of DMF.
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