Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones

Abstract

We describe the first atropselective Suzuki–Miyaura cross-coupling of β-keto enol triflates to access axially chiral (Z)-diarylmethylidene indanones (DAIs). The chemical, physical, and biological properties of DAIs are unknown, despite their being structurally similar to arylidene indanones, primarily due to the lack of racemic or chiral methods. Through this work, we demonstrate a general and efficient protocol for the racemic as well as the atropselective synthesis of (Z)-DAIs. An unusual intramolecular Morita–Baylis–Hillman reaction is utilized for the Z-selective synthesis of β-keto enol triflates.