4.8 Article

Desymmetrization of Diolefinic Diols by Enantioselective Aminothiocarbamate- Catalyzed Bromoetherification: Synthesis of Chiral Spirocycles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 20, Pages 5161-5164

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310136

Keywords

asymmetric catalysis; chemoselectivity; cyclization; furans; Lewis base

Funding

  1. National University of Singapore [143-000-509-112]
  2. A*STAR-Public Sector Funding [143-000-536-305]
  3. GSK-EDB [143-000-564-592]
  4. A*STAR

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A facile, efficient, and highly diastereo- and enantioselective bromoetherification of diolefinic diols has been developed using an amino-thiocarbamate catalyst. Further manipulations of the bromoether products enabled entry into a new class of spirocycles which are distinctively lacking in the literature.

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