Articles producció científicaQuímica Física i Inorgànica

Stereofacial Assembly of Engineered Multichiral Aziridines via B/Si Ylide Insertion

  • Identification data

    Identifier:  imarina:9469311
    Handle: https://hdl.handle.net/20.500.11797/imarina9469311
    Authors:  Pujol, M; Tarifa, L; Tarasewicz, A; Mendez, M; Fernandez, E
    Abstract:
    Halo-borylsilylcarbanion reagents can be added, with complete stereofacial control, to chiral N-tert-butanesulfinyl imines, featuring an asymmetric C-C bond, followed by concomitant intramolecular asymmetric C-N bond formation. There is exclusive access to alpha,alpha-B,Si-disubstituted aziridine units containing up to four contiguous stereocenters in a single operation. In addition, complete stereochemical discrimination has been observed in N-tert-butanesulfinyl alkyl aldimines. Post-transformation of B,Si-disubstituted aziridine generates multichiral aziridine scaffolds.

  • Others:

    Link to the original source: https://pubs.acs.org/doi/10.1021/jacsau.5c01306
    APA: Pujol, M; Tarifa, L; Tarasewicz, A; Mendez, M; Fernandez, E (2025). Stereofacial Assembly of Engineered Multichiral Aziridines via B/Si Ylide Insertion. JACS Au, 5(12), 6315-6323. DOI: 10.1021/jacsau.5c01306
    Paper original source: JACS Au. 5 (12): 6315-6323
    Article's DOI: 10.1021/jacsau.5c01306
    Journal publication year: 2025-12-22
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    Record's date: 2026-10-10
    URV's Author/s: Fernández Gutiérrez, Maria Elena
    Department: Química Física i Inorgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    Author, as appears in the article.: Pujol, M; Tarifa, L; Tarasewicz, A; Mendez, M; Fernandez, E
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Physical and theoretical chemistry, Organic chemistry, Chemistry, multidisciplinary, Chemistry (miscellaneous), Astronomia / física, Analytical chemistry
    Author's mail: mariaelena.fernandez@urv.cat

  • Keywords:

    Tert-butanesulfinyl imines
    Stereofacial control
    Si-disubstituted aziridine
    Oxetanes
    Functionalization
    Esters
    Efficient
    Chiral transmission
    B
    Aziridination
    Asymmetric-synthesis
    Alcohols
    Analytical Chemistry
    Chemistry (Miscellaneous)
    Chemistry
    Multidisciplinary
    Organic Chemistry
    Physical and Theoretical Chemistry
    Astronomia / física

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