Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of CN-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection

Ruthenium(0) Catalyzed Endiyne−α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C–C Bond Forming Transfer Hydrogenation

Upon exposure of 3,4-benzannulated 1,5-diynes (benzo-endiynes) to α-ketols (α-hydroxyketones) in the presence of Ru(0) catalysts derived from Ru₃(CO)₁₂ and RuPhos or CyJohnPhos, successive redox-triggered C–C coupling occurs to generate products of [4 + 2] cycloaddition. The proposed catalytic mechanism involves consecutive alkyne-carbonyl oxidative couplings to form transient oxaruthanacycles that suffer α-ketol mediated transfer hydrogenolysis. This process provides a new, convergent means of assembling Type II polyketide substructures

Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of CN-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection

Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of CN-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection

Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of CN-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection

Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of CN-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection

Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of CN-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection