4.8 Article

Catalytic Asymmetric Bromoetherification and Desymmetrization of Olefinic 1,3-Diols with C2-Symmetric Sulfides

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 15, Pages 5627-5630

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja5029155

Keywords

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Funding

  1. National University of Singapore [143-000-509-112]
  2. GSK-EDB [143-000-564-592]
  3. ASTAR-Public Sector Funding [143-000-536-305]
  4. NEA-ETRP [143-000-547-490]
  5. President's Graduate Fellowship

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An enantioselective and highly diastereoselective bromoetherification and desymmetrization of olefinic 1,3-diols has been developed using a C-2-symmetric cyclic sulfide catalyst. This methodology has been successfully applied to the synthesis of the key intermediate of an orally active antifungal drug posaconazole (Noxafil).

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