Asymmetric Synthesis of Cyclopenta[c]chromenones

  • Author: Angewandte Chemie International Edition
  • Published Date: 20 December 2018
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Asymmetric Synthesis of Cyclopenta[<i>c</i>]chromenones

Coumarins and related structures are commonly found in pharmaceuticals, materials, and natural products. However, catalytic enantioselective synthesis methods for chiral cyclopenta[c]-fused chromenones, which are coumarin derivatives, with high asymmetric induction had not been realized to date.

Xiang-Yu Chen, Dieter Enders, RWTH Aachen University, Germany, and colleagues have developed the first N-heterocyclic carbene (NHC)-catalyzed quadruple-domino reaction for the asymmetric synthesis of cyclopenta[c]chromenones (pictured). The team used a tetracyclic NHC derived from aminoindanol as the catalyst, tetramethylethylenediamine (TMEDA) as the base, diphenoquinone as the oxidant, lithium chloride as a cooperative Lewis acid, and 1,2-dimethoxyethane (DME) as the solvent.

The method tolerates various enals and malonates bearing an ortho-hydroxy phenyl group. The protocol enables the direct organocatalytic assembly of cyclopenta[c]-fused chromenones in good yields and with high enantioselectivities. A subsequent reductive lactone–ester conversion under ring opening allows the preparation of highly functionalized cyclopentanes.


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