252878-48-1Relevant articles and documents
Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones
Kumar, Prashant,Shirke, Rajendra P.,Yadav, Sonu,Ramasastry
, p. 4909 - 4914 (2021/06/30)
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.
Tandem Henry/oxa-Michael route to the 1,3-disubstituted-1,3-dihydrobenzo[c] furan system
Luzzio, Frederick A.,Okoromoba, Otome E.
scheme or table, p. 6530 - 6533 (2012/01/02)
The reaction of ortho-formyl cinnamates and ortho-formyl-α- benzalketones with suitably substituted alkylnitro compounds in the presence of 1,1,3,3-tetramethylguanidine results in the formation of 1,3-disubstituted dihydroisobenzofurans. The reaction mechanism entails a base-mediated nitronate addition to the aryl formyl group followed by intramolecular alcoholate addition to the unsaturated component that then affords the isobenzofuran system.
