4.8 Article

Cu(II)-Catalyzed Acylation by Thiol Esters Under Neutral Conditions: Tandem Acylation-Wittig Reaction Leading to a One-Pot Synthesis of Butenolides

Journal

ORGANIC LETTERS
Volume 12, Issue 22, Pages 5346-5349

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102407k

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Funding

  1. Program for Promotion of Basic and Applied Research for Innovations in Bio-oriented Industry (BRAIN)
  2. JSPS
  3. [19390007]
  4. [22390002]
  5. Grants-in-Aid for Scientific Research [22390002] Funding Source: KAKEN

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The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.

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