Light-Triggered Catalytic Asymmetric Allylic Benzylation with Photogenerated C-Nucleophiles | Zendy

Suva Paria | Zendy; Edoardo Carletti | Zendy; Michela Marcon | Zendy; Alessio CherubiniCelli | Zendy; Andrea Mazzanti | Zendy; Marzio Rancan | Zendy; Luca Dell’Amico | Zendy; Marcella Bonchio | Zendy; Xavier Companyó | Zendy

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Light-Triggered Catalytic Asymmetric Allylic Benzylation with Photogenerated C-Nucleophiles

Author(s) -

Suva Paria,

Edoardo Carletti,

Michela Marcon,

Alessio CherubiniCelli,

Andrea Mazzanti,

Marzio Rancan,

Luca Dell’Amico,

Marcella Bonchio,

Xavier Companyó

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c00175

Subject(s) - chemistry , nucleophile , electrophile , allylic rearrangement , stereoselectivity , catalysis , lewis acids and bases , medicinal chemistry , stereochemistry , organic chemistry

Herein is reported the asymmetric allylic benzylation of Morita-Baylis-Hillman (MBH) carbonates with 2-methylbenzophenone (MBP) derivatives as nonstabilized photogenerated C -nucleophiles. The dual activation of both reaction partners, chiral Lewis-base activation of the electrophile and light activation of the nucleophile, enables the stereoselective installation of benzyl groups at the allylic position to forge tertiary and quaternary carbon centers.

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