4.8 Article

Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations

Journal

CHEMICAL SCIENCE
Volume 6, Issue 6, Pages 3550-3555

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc00753d

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Funding

  1. EPSRC
  2. AstraZeneca
  3. Pfizer
  4. University of Edinburgh
  5. University of Nottingham
  6. EPSRC [EP/I004769/1, EP/I004769/2] Funding Source: UKRI
  7. Engineering and Physical Sciences Research Council [EP/I004769/2, EP/I004769/1] Funding Source: researchfish

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2,2-Disubstituted cyclic 1,3-diketones containing a tethered electron-deficient alkene undergo chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations to give bridged bicyclic products in high enantioselectivities. Both bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes are accessible using this methodology.

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