4.8 Article

Chiral Phosphine-Silver(I) Complex Catalyzed Enantioselective Interrupted Feist-Benary Reaction with Ynones: The Aldol-Cycloisomerization Cascade

Journal

ORGANIC LETTERS
Volume 17, Issue 13, Pages 3302-3305

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01468

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Funding

  1. DST, India, through J. C. Bose Fellowship
  2. IISER Bhopal

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Silver-catalyzed interrupted Feist-Benary reaction is described for the efficient enantioselective synthesis of dihydrofuran heterocycles. A new method has been developed for the silver(I)-(R)-BINAP complex mediated aldol cycloisomerization cascade reaction between ynones and 1,3-diketones to provide functionalized dihydrofurans with moderate to good yields (up to 95%) and good to excellent enantiomeric excess (up to 98%). The presence of an exocyclic double bond and hydroxy group in the dihydrofuran products provides wide scope for further structural manipulation.

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