Central-to-Axial Chirality: Asymmetric Organocatalytic Synthesis of Axially Chiral Chalcones via Exocyclic Dihydronaphthalenes

Abstract

Asymmetric synthesis of an unprecedented exocyclic dihydronaphthalene and an axially chiral naphthalene chalcone has been disclosed. Good to excellent asymmetric induction is achieved. The success is attributed to the unusual formation of exocyclic dihydronaphthalene, which plays a crucial role in ensuring axial chirality. This is the first report of exocyclic molecules capable of enabling the synthesis of axially chiral chalcones via stepwise asymmetric vinylogous domino double-isomerization using secondary amine catalysis.

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