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Highly enantioselective 1,6-addition of dienolates to coumarins and chromones through N-heterocyclic carbene catalysis

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Abstract

Coumarins and chromones are privileged motifs in natural products and pharmaceuticals; yet, the challenge of devising an asymmetric strategy for their δ-functionalization has remained unsolved to date. In the past three years, 1,6-addition provided new possibilities for N-heterocyclic carbene (NHC) catalyzed asymmetric carbon–carbon bond formation. However, the corresponding formal [4 + 2] cycloadditions via 1,6-addition of dienolates are far less developed. We demonstrate herein the first γ,δ-difunctionalization of cyanocoumarins and nitrochromones via NHC-catalyzed 1,6-addition of dienolates. This strategy allows the synthesis of two valuable classes of compounds in high stereoselectivities with a broad scope.

Graphical abstract: Highly enantioselective 1,6-addition of dienolates to coumarins and chromones through N-heterocyclic carbene catalysis

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Article information


Submitted
10 Aug 2020
Accepted
10 Oct 2020
First published
12 Oct 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Highly enantioselective 1,6-addition of dienolates to coumarins and chromones through N-heterocyclic carbene catalysis

Q. Liu, Z. Wang and X. Chen, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00963F

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