4.7 Article

Expanding the Scope of the Organocatalytic Addition of Fluorobis(phenylsulfonyl)methane to Enals: Enantioselective Cascade Synthesis of Fluoroindane and Fluorochromanol Derivatives

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 2-3, Pages 437-446

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300703

Keywords

enantioselectivity; fluorine; indanes; Michael reaction; organocatalysis

Funding

  1. Spanish Ministry of Science and Innovation (MICINN) [AYA2009-13920-C02-02]
  2. MICINN
  3. China Scholarship Council
  4. NRF Nano.Material Technology Development Program [2012M3A7B4049652]
  5. NRF Basic Science Research Program [2009-0094023]
  6. COST Action [CM0905]
  7. European Regional Development Fund (ERDF) (AI-Chem InterReg IVb)

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Highly enantioselective cascade reactions for the synthesis of fluoroindanes and chromanols derivatives are described. The cascade reactions consisted of either a double Michael reaction or Michael-hemiacetal formation via the addition of fluorobis(phenylsulfonyl) methane (FBSM) to enals. The final products were obtained in good yields with excellent stereoselectivities.

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