Nickel-Catalyzed Asymmetric Addition of Aromatic Halides to Ketones: Highly Enantioselective Synthesis of Chiral 2,3-Dihydrobenzofurans Containing a Tertiary Alcohol
Ying Li, Wendian Li, Jiangyan Tian, Guozheng Huang, Hui Lv
Abstract
A highly enantioselective and straightforward synthetic procedure to chiral 3-hydroxy-2,3-dihydrobenzofurans has been developed by nickel/bisoxazoline-catalyzed intramolecular asymmetric addition of aryl halides to unactivated ketones, giving 2,3-dihydrobenzofurans with a chiral tertiary alcohol at the C-3 position in good yields and excellent enantioselectivities (up to 92% yield and 98% ee). The gram-scale reaction also proceeded smoothly without a loss of yield and enantioselectivity.
Topics & Concepts
ChemistryEnantioselective synthesisHalideYield (engineering)Intramolecular forceCatalysisAlcoholNickelArylTertiary alcoholsOrganic chemistryMedicinal chemistryCombinatorial chemistryAlkylMetallurgyMaterials scienceAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization Methods