Asymmetric three-component Tsuji–Trost allylation reaction enabled by chiral aldehyde/palladium combined catalysis

Liu, Jian-Hua; Wen, Wei; Wu, Zhu-Lian; Cai, Tian; Huang, Yan-Min; Guo, Qi-Xiang

doi:10.1039/d4sc02594f

Chem. Sci.

2024

DOI: 10.1039/d4sc02594f

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Asymmetric three-component Tsuji–Trost allylation reaction enabled by chiral aldehyde/palladium combined catalysis

Jian-Hua Liu,

Wei Wen,

Zhu-Lian Wu

et al.

Abstract: An asymmetric three-component allylation reaction is achieved under the promotion of chiral aldehyde/palladium combined catalysis via mixed Heck/allylation cascades.

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Enantioselective Three‐Component α‐Allylic Alkylation of α‐Amino Esters by Synergistic Photoinduced Pd/Carbonyl Catalysis

Han,

Yi,

Ding

et al. 2024

Angewandte Chemie

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Photoinduced excited‐state Pd catalysis has emerged as an intriguing strategy for unlocking new reactivity potential of simple substrates. However, the related transformations are still limited and the enantiocontrol remains challenging. Organocatalysis displays unique capability in substrate activation and stereocontrol. Combination of organocatalysis and photoinduced excited‐state Pd catalysis may provide opportunities to develop new enantioselective reactions from simple substrates. By applying cooperative triple catalysis including excited‐state Pd catalysis, ground‐state Pd catalysis, and carbonyl catalysis, we have successfully realized enantioselective α‐allylic alkylation of α‐amino esters with simple styrene and alkyl halide starting materials. The reaction allows rapid modular assembly of the three reaction partners into a variety of chiral quaternary α‐amino esters in good yields with 90‐99% ee, without protecting group manipulations at the active NH2 group. The cooperation of the chiral pyridoxal catalyst and the chiral phosphine ligand accounts for the excellent chirality induction.

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Enantioselective Three‐Component α‐Allylic Alkylation of α‐Amino Esters by Synergistic Photoinduced Pd/Carbonyl Catalysis

Han,

Yi,

Ding

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Enantioselective Three‐Component α‐Allylic Alkylation of α‐Amino Esters by Synergistic Photoinduced Pd/Carbonyl Catalysis

Han,

Yi,

Ding

et al. 2024

Angew Chem Int Ed

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show abstract

Asymmetric Synthesis of α,α-Disubstituted α-Amino Acid Esters via Tsuji–Trost Allylation

2024

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Asymmetric three-component Tsuji–Trost allylation reaction enabled by chiral aldehyde/palladium combined catalysis

Abstract: An asymmetric three-component allylation reaction is achieved under the promotion of chiral aldehyde/palladium combined catalysis via mixed Heck/allylation cascades.

Cited by 3 publications

References 50 publications

Enantioselective Three‐Component α‐Allylic Alkylation of α‐Amino Esters by Synergistic Photoinduced Pd/Carbonyl Catalysis

Enantioselective Three‐Component α‐Allylic Alkylation of α‐Amino Esters by Synergistic Photoinduced Pd/Carbonyl Catalysis

Enantioselective Three‐Component α‐Allylic Alkylation of α‐Amino Esters by Synergistic Photoinduced Pd/Carbonyl Catalysis

Asymmetric Synthesis of α,α-Disubstituted α-Amino Acid Esters via Tsuji–Trost Allylation

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