Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates

Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates.

An enantioselective dearomatization of isoquinolines has been developed using chiral anion-binding catalysis. This transformation, catalyzed by a simple and easy to prepare tert-leucine-based thiourea derivative, makes use of silyl phosphite as a nucleophile and generates cyclic α-aminophosphonates. This is the first time asymmetric anion-binding catalysis has been applied to the synthesis of α...

Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates† †Electronic supplementary information (ESI) available: Experimental details, characterization and analytical data. CCDC 1476699 (4w). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc02466a Click here for additional data file. Click here for additional data file.

Chiral anion phase-transfer catalysis applied to the direct enantioselective fluorinative dearomatization of phenols.

Chiral anion phase-transfer catalysis has enabled the direct and highly enantioselective fluorinative dearomatization of phenols catalyzed by a BINOL-derived phosphate. The process efficiently transforms simple, readily available phenols into fluorinated chiral small molecules bearing reactive functionality under ambient reaction conditions with high enantioselectivity. The close relationship o...

Enantioselective hydrogenation of isoquinolines.

Asymmetric hydrogenation of (hetero)arenes is one of the most straightforward ways to synthesize enantiomerically pure, saturated or partially saturated cyclic molecules. Recent progress has significantly expanded the substrate scope of this reaction. Whereas a number of highly efficient catalytic systems have been found for the asymmetric hydrogenation of quinolines, structurally related isoqu...

Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates.

The first example of an asymmetric organocatalyzed decarboxylative aldol reaction of β-ketoacids (aroylacetic acids) with α-ketophosphonates that produces a quaternary chiral centre has been developed. A quinidine based bifunctional urea derivative was identified as the preferred catalyst affording γ-aroyl tertiary α-hydroxyphosphonates in good yield and enantioselectivity. The 31P NMR spectros...