Visible Light-PromotedDeracemization of α‑AminoAldehyde by Synergistic Chiral Primary Amine and Hypervalent IodineCatalysis

α-Amino aldehydes, as versatile chiral synthons, are easily racemized under normal acid or base conditions, seriously limiting their synthetic potentials. We report herein an effective deracemization of α-amino aldehydes by a synergistic chiral primary amine and hypervalent iodine catalysis under visible light. The developed catalytic system allows for the on-demand production of α-Boc- or Cbz-protected amino aldehydes with high enantioselectivity. Mechanistic studies verified a photochemical <i>Z</i>–<i>E</i> isomerization mechanism that drives the deracemization process.

Publication Details

Journal
Figshare
Published
2025-02-07
DOI
https://doi.org/10.1021/jacs.4c18407.s001
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
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0.00
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article

Visible Light-PromotedDeracemization of α‑AminoAldehyde by Synergistic Chiral Primary Amine and Hypervalent IodineCatalysis

Figshare
Oxidative Organic Chemistry Reactions
article

Visible Light-PromotedDeracemization of α‑AminoAldehyde by Synergistic Chiral Primary Amine and Hypervalent IodineCatalysis

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Abstract

α-Amino aldehydes, as versatile chiral synthons, are easily racemized under normal acid or base conditions, seriously limiting their synthetic potentials. We report herein an effective deracemization of α-amino aldehydes by a synergistic chiral primary amine and hypervalent iodine catalysis under visible light. The developed catalytic system allows for the on-demand production of α-Boc- or Cbz-protected amino aldehydes with high enantioselectivity. Mechanistic studies verified a photochemical <i>Z</i>–<i>E</i> isomerization mechanism that drives the deracemization process.

Figshare
Openalex Percentile: Top 63%
Oxidative Organic Chemistry Reactions
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Visible Light-PromotedDeracemization of α‑AminoAldehyde by Synergistic Chiral Primary Amine and Hypervalent IodineCatalysis · Figshare (2025) | TGRS Research Map | TGRS