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

ABSTRACT: 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.

SUBMITTER: Paria S

PROVIDER: S-EPMC7997570 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Light-Triggered Catalytic Asymmetric Allylic Benzylation with Photogenerated <i>C</i>-Nucleophiles.

Paria Suva S Carletti Edoardo E Marcon Michela M Cherubini-Celli Alessio A Mazzanti Andrea A Rancan Marzio M Dell'Amico Luca L Bonchio Marcella M Companyó Xavier X

The Journal of organic chemistry 20200303 6

Herein is reported the asymmetric allylic benzylation of Morita-Baylis-Hillman (MBH) carbonates with 2-methylbenzophenone (MBP) derivatives as nonstabilized photogenerated <i>C</i>-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. ...[more]

PMID: 32081000

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