Catalytic enantioselective synthesis of chiral phthalides by efficient reductive cyclization of 2-acylarylcarboxylates under aqueous transfer hydrogenation conditions.
A new diamine ligand for asymmetric transfer hydrogenation (ATH) was discovered. The reductive cyclization of 2-acylarylcarboxylates was found to proceed highly stereoselectively by the new Ru complex-catalyzed ATH and subsequent in situ lactonization under aqueous conditions. It enables efficient access to a wide variety of 3-substituted phthalides in enantiomerically pure form.
Zhang
Bo
B
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Xu
Ming-Hua
MH
Lin
Guo-Qiang
GQ
D001572:Benzofurans / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003959:Diamines / Q000737:chemistry; D006865:Hydrogenation; D008024:Ligands; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014867:Water / Q000737:chemistry*
D001572:Benzofurans; D002264:Carboxylic Acids; D003959:Diamines; D008024:Ligands; D014867:Water; D012428:Ruthenium; C082022:phthalide