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Type II Anion Relay Chemistry: Exploiting Bifunctional Weinreb Amide Linchpins for the One-Pot Synthesis of Differentiated 1,3-Diketones, Pyrans, and Spiroketals.

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  • المؤلفون: Farrell M;Farrell M; Melillo B; Melillo B; Smith AB 3rd; Smith AB 3rd
  • المصدر:
    Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2016 Jan 04; Vol. 55 (1), pp. 232-5. Date of Electronic Publication: 2015 Nov 20.
  • نوع النشر :
    Journal Article; Research Support, N.I.H., Extramural
  • اللغة:
    English
  • معلومة اضافية
    • المصدر:
      Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE
    • بيانات النشر:
      Publication: <2004-> : Weinheim : Wiley-VCH
      Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
    • الموضوع:
      Amides/*chemistry ; Ketones/*chemical synthesis ; Pyrans/*chemical synthesis ; Spiro Compounds/*chemical synthesis; Anions/chemical synthesis ; Anions/chemistry ; Ketones/chemistry ; Molecular Structure ; Pyrans/chemistry ; Spiro Compounds/chemistry
    • نبذة مختصرة :
      The design, synthesis, and validation of new highly effective bifunctional linchpins for type II anion relay chemistry (ARC) has been achieved. The mechanistically novel negative-charge migration that comprises the Brook rearrangement is now initiated by a stabilized tetrahedral intermediate, which is generated by nucleophilic addition to a Weinreb amide, rather than by a simple oxyanion that is generated from an epoxide. As a result, the linchpin preserves the carbonyl functionality in the ARC adducts, thus permitting access to functionally complex systems in a single flask without the need for further chemical manipulations. This tactic was validated with the one-pot preparation of monoprotected 1,3-diketones as well as pyran and spiroketal scaffolds, depending on the choice of nucleophile, electrophile, and work-up conditions.
      (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
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    • Grant Information:
      R01 GM029028 United States GM NIGMS NIH HHS; GM-29028 United States GM NIGMS NIH HHS
    • Contributed Indexing:
      Keywords: 1,3-diketones; Brook rearrangement; Weinreb amides; anion relay chemistry; spiroketals
    • الرقم المعرف:
      0 (Amides)
      0 (Anions)
      0 (Ketones)
      0 (Pyrans)
      0 (Spiro Compounds)
    • الموضوع:
      Date Created: 20151121 Date Completed: 20160916 Latest Revision: 20181113
    • الموضوع:
      20240829
    • الرقم المعرف:
      PMC4726982
    • الرقم المعرف:
      10.1002/anie.201509342
    • الرقم المعرف:
      26586577