Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes
Top Cited Papers
Open Access
- 23 June 2015
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 137 (25) , 8069-8077
Abstract
A versatile method for the rapid synthesis of diverse enantiomerically enriched lactones has been developed based on Cu-catalyzed enantioselective radical oxyfunctionalization of alkenes. The scope of this strategy encompasses a series of enantioselective difunctionalization reactions: oxyazidation, oxysulfonylation, oxyarylation, diacyloxylation, and oxyalkylation. These reactions provide straightforward access to a wide range of useful chiral lactone building blocks containing tetrasubstituted stereogenic centers, which are hard to access traditionally.Keywords
Funding Information
- National Institute of General Medical Sciences (GM58160)
This publication has 118 references indexed in Scilit:
- Combined Oxypalladation/C-H Functionalization: Palladium(II)‐Catalyzed Intramolecular Oxidative Oxyarylation of HydroxyalkenesAngewandte Chemie International Edition, 2012
- Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-CouplingsJournal of the American Chemical Society, 2011
- Copper‐Catalyzed Trifluoromethylation of Unactivated OlefinsAngewandte Chemie International Edition, 2011
- Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic ApplicationsChemical Reviews, 2011
- Preparative and Mechanistic Studies toward the Rational Development of Catalytic, Enantioselective Selenoetherification ReactionsJournal of the American Chemical Society, 2010
- Tertiary Aminourea‐Catalyzed Enantioselective IodolactonizationAngewandte Chemie International Edition, 2010
- Asymmetric Palladium-Catalyzed Carboamination Reactions for the Synthesis of Enantiomerically Enriched 2-(Arylmethyl)- and 2-(Alkenylmethyl)pyrrolidinesJournal of the American Chemical Society, 2010
- Copper‐Promoted and Copper‐Catalyzed Intermolecular Alkene DiaminationAngewandte Chemie International Edition, 2010
- Gold-Catalyzed Three-Component Coupling: Oxidative Oxyarylation of AlkenesJournal of the American Chemical Society, 2010
- Synthesis and Preliminary Biological Studies of 3-Substituted Indoles Accessed by a Palladium-Catalyzed Enantioselective Alkene Difunctionalization ReactionJournal of the American Chemical Society, 2010