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  1. Article: Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry.

    Gorelik, Daniel J / Desai, Shrey P / Jdanova, Sofia / Turner, Julia A / Taylor, Mark S

    Chemical science

    2024  Volume 15, Issue 4, Page(s) 1204–1236

    Abstract: This review article highlights the diverse ways in which recent developments in the areas of photocatalysis and visible light photochemistry are impacting synthetic carbohydrate chemistry. The major topics covered are photocatalytic glycosylations, ... ...

    Abstract This review article highlights the diverse ways in which recent developments in the areas of photocatalysis and visible light photochemistry are impacting synthetic carbohydrate chemistry. The major topics covered are photocatalytic glycosylations, generation of radicals at the anomeric position, transformations involving radical formation at non-anomeric positions, additions to glycals, processes initiated by photocatalytic hydrogen atom transfer from sugars, and functional group interconversions at OH and SH groups. Factors influencing stereo- and site-selectivity in these processes, along with mechanistic aspects, are discussed.
    Language English
    Publishing date 2024-01-02
    Publishing country England
    Document type Journal Article ; Review
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/d3sc05400d
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Catalyst-Controlled, Site-Selective Sulfamoylation of Carbohydrate Derivatives.

    Gorelik, Daniel J / Turner, Julia A / Taylor, Mark S

    Organic letters

    2022  Volume 24, Issue 29, Page(s) 5249–5253

    Abstract: Methods for site-selective sulfamoylation of secondary hydroxyl groups in pyranosides are described. Using a boronic acid catalyst, selective installation of a Boc-protected sulfamoyl group at the equatorial position ... ...

    Abstract Methods for site-selective sulfamoylation of secondary hydroxyl groups in pyranosides are described. Using a boronic acid catalyst, selective installation of a Boc-protected sulfamoyl group at the equatorial position of
    MeSH term(s) Alcohols ; Boronic Acids ; Carbohydrates ; Catalysis
    Chemical Substances Alcohols ; Boronic Acids ; Carbohydrates
    Language English
    Publishing date 2022-06-21
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.2c01590
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Catalyst-Controlled, Site-Selective Sulfamoylation of Carbohydrate Derivatives

    Gorelik, Daniel J. / Turner, Julia A. / Taylor, Mark S.

    Organic letters. 2022 June 22, v. 24, no. 29

    2022  

    Abstract: Methods for site-selective sulfamoylation of secondary hydroxyl groups in pyranosides are described. Using a boronic acid catalyst, selective installation of a Boc-protected sulfamoyl group at the equatorial position of cis-diols in manno- and galacto- ... ...

    Abstract Methods for site-selective sulfamoylation of secondary hydroxyl groups in pyranosides are described. Using a boronic acid catalyst, selective installation of a Boc-protected sulfamoyl group at the equatorial position of cis-diols in manno- and galacto-configured substrates has been achieved. Activation of trans-diol groups in gluco- and galacto-configured substrates is also possible by employing an organotin catalyst.
    Keywords boronic acids ; carbohydrates ; catalysts
    Language English
    Dates of publication 2022-0622
    Size p. 5249-5253.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.2c01590
    Database NAL-Catalogue (AGRICOLA)

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  4. Article ; Online: Photocatalytic, site-selective oxidations of carbohydrates.

    Gorelik, Daniel J / Dimakos, Victoria / Adrianov, Timur / Taylor, Mark S

    Chemical communications (Cambridge, England)

    2021  Volume 57, Issue 91, Page(s) 12135–12138

    Abstract: Site-selective oxidations of carbohydrates, employing acridinium photocatalysis and quinuclidine hydrogen atom transfer catalysis, are presented. Protocols have been developed for oxidations of all-equatorial carbohydrates as well as those ... ...

    Abstract Site-selective oxidations of carbohydrates, employing acridinium photocatalysis and quinuclidine hydrogen atom transfer catalysis, are presented. Protocols have been developed for oxidations of all-equatorial carbohydrates as well as those containing
    Language English
    Publishing date 2021-11-16
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d1cc05124e
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article: Photocatalytic, site-selective oxidations of carbohydrates

    Gorelik, Daniel J. / Dimakos, Victoria / Adrianov, Timur / Taylor, Mark S.

    Chemical communications. 2021 Nov. 16, v. 57, no. 91

    2021  

    Abstract: Site-selective oxidations of carbohydrates, employing acridinium photocatalysis and quinuclidine hydrogen atom transfer catalysis, are presented. Protocols have been developed for oxidations of all-equatorial carbohydrates as well as those containing cis- ...

    Abstract Site-selective oxidations of carbohydrates, employing acridinium photocatalysis and quinuclidine hydrogen atom transfer catalysis, are presented. Protocols have been developed for oxidations of all-equatorial carbohydrates as well as those containing cis-1,2-diols. Site-selectivity reflects the relative rates of hydrogen atom transfer from the carbohydrate C–H bonds, and can be enhanced using a phosphate hydrogen-bonding or boronic acid catalyst.
    Keywords boronic acids ; carbohydrates ; catalysts ; hydrogen ; hydrogen bonding ; phosphates ; photocatalysis
    Language English
    Dates of publication 2021-1116
    Size p. 12135-12138.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d1cc05124e
    Database NAL-Catalogue (AGRICOLA)

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  6. Article ; Online: Site- and Stereoselective C-H Alkylations of Carbohydrates Enabled by Cooperative Photoredox, Hydrogen Atom Transfer, and Organotin Catalysis.

    Gorelik, Daniel J / Turner, Julia A / Virk, Tarunpreet S / Foucher, Daniel A / Taylor, Mark S

    Organic letters

    2021  Volume 23, Issue 13, Page(s) 5180–5185

    Abstract: Diorganotin dihalides act as cocatalysts for site-selective and stereoselective couplings of diol-containing carbohydrates with electron-deficient alkenes in the presence of an Ir(III) photoredox catalyst and quinuclidine, a hydrogen atom transfer ... ...

    Abstract Diorganotin dihalides act as cocatalysts for site-selective and stereoselective couplings of diol-containing carbohydrates with electron-deficient alkenes in the presence of an Ir(III) photoredox catalyst and quinuclidine, a hydrogen atom transfer mediator. Quantum-chemical calculations support a proposed mechanism involving the formation of a cyclic stannylene acetal intermediate that shows enhanced reactivity toward hydrogen atom abstraction by the quinuclidinium radical cation. Addition of the carbon-centered radical to the alkene partner results in
    Language English
    Publishing date 2021-06-16
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.1c01718
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: Site- and Stereoselective C–H Alkylations of Carbohydrates Enabled by Cooperative Photoredox, Hydrogen Atom Transfer, and Organotin Catalysis

    Gorelik, Daniel J. / Turner, Julia A. / Virk, Tarunpreet S. / Foucher, Daniel A. / Taylor, Mark S.

    Organic letters. 2021 June 16, v. 23, no. 13

    2021  

    Abstract: Diorganotin dihalides act as cocatalysts for site-selective and stereoselective couplings of diol-containing carbohydrates with electron-deficient alkenes in the presence of an Ir(III) photoredox catalyst and quinuclidine, a hydrogen atom transfer ... ...

    Abstract Diorganotin dihalides act as cocatalysts for site-selective and stereoselective couplings of diol-containing carbohydrates with electron-deficient alkenes in the presence of an Ir(III) photoredox catalyst and quinuclidine, a hydrogen atom transfer mediator. Quantum-chemical calculations support a proposed mechanism involving the formation of a cyclic stannylene acetal intermediate that shows enhanced reactivity toward hydrogen atom abstraction by the quinuclidinium radical cation. Addition of the carbon-centered radical to the alkene partner results in C-alkylation of the carbohydrate substrate.
    Keywords alkenes ; alkylation ; carbohydrates ; catalysts ; catalytic activity ; cations ; hydrogen ; redox reactions ; stereoselectivity
    Language English
    Dates of publication 2021-0616
    Size p. 5180-5185.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.1c01718
    Database NAL-Catalogue (AGRICOLA)

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    Inter-library loan at ZB MED

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