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

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

doi:10.1039/d1sc00760b

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

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

25 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 language	English
Pages (from-to)	5892-5897
Number of pages	6
Journal	Chemical Science
Volume	12
Issue number	16
DOIs	https://doi.org/10.1039/d1sc00760b
State	Published - 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.

Access to Document

10.1039/d1sc00760b

Cite this

@article{c8f0028f9a274a889a18e91715c6f7a6,

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

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.",

author = "Chung, {Da Sol} and Park, {Steve H.} and Lee, {Sang Gi} and Hyunwoo Kim",

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: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = apr,

day = "28",

doi = "10.1039/d1sc00760b",

language = "English",

volume = "12",

pages = "5892--5897",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "16",

}

TY - JOUR

T1 - Electrochemically driven stereoselective approach tosyn-1,2-diol derivatives from vinylarenes and DMF

AU - Chung, Da Sol

AU - Park, Steve H.

AU - Lee, Sang Gi

AU - Kim, Hyunwoo

N1 - 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.

PY - 2021/4/28

Y1 - 2021/4/28

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85105160663&partnerID=8YFLogxK

U2 - 10.1039/d1sc00760b

DO - 10.1039/d1sc00760b

M3 - Article

AN - SCOPUS:85105160663

SN - 2041-6520

VL - 12

SP - 5892

EP - 5897

JO - Chemical Science

JF - Chemical Science

IS - 16

ER -

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

Abstract

Bibliographical note

Access to Document

Fingerprint

Cite this