Alkylation of\nGlycine Derivatives through a Synergistic\nSingle-Electron Transfer and Halogen-Atom Transfer Process

Here, we present a versatile method for forming C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bonds, enabling the synthesis of\na range\nof natural and non-natural amino acids. This approach utilizes readily\navailable glycine derivatives and alkyl iodides, combining single-electron\ntransfer and halogen-atom transfer processes. The utility of this\nstep-economic and redox-economic C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bond formation is further highlighted in the late-stage\nsite-selective modifications of the glycine residue in short peptides.

Publication Details

Journal
Figshare
Published
2024-08-29
DOI
https://doi.org/10.1021/acs.orglett.4c02352.s001
Primary Topic
Chemical Synthesis and Analysis
Type
article
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article

Alkylation of\nGlycine Derivatives through a Synergistic\nSingle-Electron Transfer and Halogen-Atom Transfer Process

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Chemical Synthesis and Analysis
article

Alkylation of\nGlycine Derivatives through a Synergistic\nSingle-Electron Transfer and Halogen-Atom Transfer Process

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Abstract

Here, we present a versatile method for forming C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bonds, enabling the synthesis of\na range\nof natural and non-natural amino acids. This approach utilizes readily\navailable glycine derivatives and alkyl iodides, combining single-electron\ntransfer and halogen-atom transfer processes. The utility of this\nstep-economic and redox-economic C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bond formation is further highlighted in the late-stage\nsite-selective modifications of the glycine residue in short peptides.

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Openalex Percentile: Top 73%
Chemical Synthesis and Analysis
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Alkylation of\nGlycine Derivatives through a Synergistic\nSingle-Electron Transfer and Halogen-Atom Transfer Process · Figshare (2024) | TGRS Research Map | TGRS