Electrochemically driven stereoselective approach tosyn-1,2-diol derivatives from vinylarenes and DMF

Da Sol Chung, Steve H. Park, Sang Gi Lee, Hyunwoo Kim

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

We have developed an electrochemically driven strategy for the stereoselective synthesis of protectedsyn-1,2-diols from vinylarenes withN,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 protectedsyn-1,2-diols in a single step. This reaction proceedsviaan 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 asyn-diastereoselectivity upon the second nucleophilic attack of DMF.

Original languageEnglish
Pages (from-to)5892-5897
Number of pages6
JournalChemical Science
Volume12
Issue number16
DOIs
StatePublished - 28 Apr 2021

Bibliographical note

Funding Information:
This work was supported the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) [NRF-2021R1C1C1004605 (H. Kim)]. D. S. Chung acknowledges the National Research Foundation (NRF-2019R1A6A3A13096586). This study made use of the NMR facility supported by Korea Basic Science Institute (National Research Facilities and Equipment Center) grant funded by the Ministry of Education (NRF-2020R1A6C101B194).

Publisher Copyright:
© The Royal Society of Chemistry 2021.

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