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Divergent and consecutive skeletal editing of saturated primary amines.

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  • Author(s): Li LH;Li LH; Su S; Su S; Zheng X; Zheng X; Zhang L; Zhang L
  • Source:
    Science (New York, N.Y.) [Science] 2026 Apr 30; Vol. 392 (6797), pp. 528-535. Date of Electronic Publication: 2026 Apr 30.
  • Publication Type:
    Journal Article
  • Language:
    English
  • Additional Information
    • Source:
      Publisher: American Association for the Advancement of Science Country of Publication: United States NLM ID: 0404511 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1095-9203 (Electronic) Linking ISSN: 00368075 NLM ISO Abbreviation: Science Subsets: MEDLINE
    • Publication Information:
      Publication: : Washington, DC : American Association for the Advancement of Science
      Original Publication: New York, N.Y. : [s.n.] 1880-
    • Subject Terms:
      Amines*/chemistry ; Heterocyclic Compounds*/chemistry ; Heterocyclic Compounds*/chemical synthesis; Nitrogen/chemistry ; Biological Products/chemistry ; Iodine/chemistry ; Oxidation-Reduction ; Stereoisomerism
    • Abstract:
      Given the prevalence of nitrogen heterocycles in pharmaceuticals, divergent skeletal editing techniques that enable rapid access to a diverse library of azacycles from a single substrate are highly desirable. Herein, we report a skeletal editing approach that converts abundant saturated primary amines into N-heterocycles, with exceptional functional-group compatibility, broad skeletal diversity, superior regioselectivity, and diastereospecificity (both >20:1). By harnessing the reactivity of hypervalent iodines, an imino ether intermediate is generated through mild iodane-mediated oxidation, facile N-internalization, and methoxy anion addition. This pivotal intermediate serves as a versatile platform capable of interception by a wide spectrum of nucleophiles, thereby enabling the generation of structurally diverse nitrogen heterocycles (>15 classes). Furthermore, this strategy enables challenging site-controlled carbon-to-nitrogen transmutation and ring contraction of natural products through a one-pot, consecutive skeletal editing sequence.
    • Comments:
      Comment in: Science. 2026 Apr 30;392(6797):470. doi: 10.1126/science.aeh2468.. (PMID: 42060767)
    • Accession Number:
      0 (Amines)
      0 (Heterocyclic Compounds)
      N762921K75 (Nitrogen)
      0 (Biological Products)
      9679TC07X4 (Iodine)
    • Publication Date:
      Date Created: 20260430 Date Completed: 20260430 Latest Revision: 20260501
    • Publication Date:
      20260502
    • Accession Number:
      10.1126/science.aee5416
    • Accession Number:
      42060759