A C₂-Symmetric Chiral Bis-Sulfoxide Ligand in a Rhodium-Catalyzed Reaction: Asymmetric 1,4-Addition of Sodium Tetraarylborates to Chromenones

Citations Over TimeTop 10% of 2010 papers

Abstract

A new C2-symmetric chiral bis-sulfoxide ligand, (R,R)-1,2-bis(tert-butylsulfinyl)benzene, has been designed and prepared by the reaction of (R)-benzyl tert-butylsulfoxide with (R)-thiosulfinate. This ligand exhibits excellent enantioselectivities in the Rh-catalyzed asymmetric 1,4-addition reaction. In particular, the present work has realized access to optically pure flavanones for the first time through 1,4-addition of arylboronic reagents to chromenones.

Related Papers

• → Palladium(II)-Catalyzed Enantioselective C(sp3)–H Activation Using a Chiral Hydroxamic Acid Ligand(2014)259 cited
• → Enantioselective Hydrogenation of Diarylmethanimines for Synthesis of Chiral Diarylmethylamines(2016)41 cited
• → C 2-Symmetric Chiral Sulfoxide-Mediated Intermolecular Interrupted Pummerer Reaction for Enantioselective Construction of C3a-Substituted Pyrroloindolines(2016)28 cited
• → Isosterically designed chiral catalysts: Rationale, optimization and their application in enantioselective nucleophilic addition to aldehydes(2020)10 cited
• → 3,3′-dinitro-octahydrobinaphthol: A new chiral ligand for metal-catalyzed enantioselective reactions(1997)52 cited