4.7 Article

Enantioselective Cascade Oxa-Michael-Michael Reactions of 2-Hydroxynitrostyrenes with Enones Using a Prolinol Thioether Catalyst

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 8, Pages 1753-1760

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201301114

Keywords

asymmetric catalysis; domino reactions; functionalized chromanes; functionalized tetrahydroxanthenones; organocatalysis

Funding

  1. NSFC [21202149]
  2. Zhejiang Natural Science Foundation [Y4110348]
  3. Foundation of Zhejiang Education Committee [Y201225109]
  4. Foundation of Zhejiang Key Course of Chemical Engineering and Technology

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The efficient simultaneous activation of cyclohexenones or simple alkyl acyclic enones and 2-hydroxynitrostyrenes was realized by using a prolinol thioether catalyst. Thus, a highly chemo-, diastereo- and enantioselective synthesis of functionalized tetrahydroxanthenones and chromanes with up to three contiguous stereocenters was developed.

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