4.7 Article

Rapid Construction of Polycyclic Ketones and the Divergent Kinetic Resolution Using Ruthenium-Catalyzed Transfer Hydrogenation

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 8, Pages 2071-2077

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001594

Keywords

Annulation; Michael addition; ruthenium complex; transfer hydrogenation; stereodivergent resolution

Funding

  1. NSFC [21871260, 22071242]
  2. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  3. Fujian Natural Science Foundation [2018J05035]
  4. China Postdoctoral Science Foundation [2018M630734]

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A unique cascade sequence using dienone substrates was reported for the first time, allowing rapid construction of 5/6/5 fused ring compounds with good to high stereoselectivities under mild conditions. Enantioenriched polycyclic rings can be obtained with high enantioselectivity using ruthenium-catalyzed transfer hydrogenation, providing a concise approach for the construction of related fused ring substances.
A unique cascade sequence of vinylogous Michael addition-Michael addition-oxa-Michael addition using dienone substrates was reported for the first time, achieving the rapid construction of 5/6/5 fused ring compounds in good yields with good to high stereoselectivities under mild conditions. Enantioenriched polycyclic rings can be obtained with high level of enantioselectivity by the stereodivergent resolution using ruthenium-catalyzed transfer hydrogenation. The protocol provides a concise approach for the construction of the related fused ring substances.

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