Redox transformation of β-sulfinyl esters for asymmetric synthesis of sulfone-based axially chiral styrenes

Abstract

Sulfenate anions are always in-situ generated from β-sulfinyl esters in catalytic asymmetric sulfinylation, while the potential oxidative transformation remains underdeveloped. Herein, an unprecedented redox transformation of β-sulfinyl esters has been...

Aromatic Amine and Chiral Phosphoric Acid Synergistic Catalyzed Cascade Reaction of Alkynylnaphthols with Aldehydes

“…Different with the π complexation model in transition-metal-catalyzed reactions with alkynes, noncovalent interaction with substituted alkynes is a common activation model in organocatalysis. The addition of active electrophiles such as protons and halogens to the alkynes in the aid of organic bases or acids would first generate ortho -quinone methides, , followed by intermolecular/intramolecular addition of the other nucleophiles to complete the reaction (Scheme a). Organocatalysts play a key role during these processes by employing dual hydrogen bond activation modes with the hydroxyl group and electrophiles.…”

Generation of sulfones utilizing β-sulfinyl esters as masked aryl sulfinates under redox-neutral conditions

“…16 Interestingly, very recently, Zhao and co-workers have achieved copper catalysed sulfone generation using β-sulfinyl esters and vinylidene o -quinone methide intermediates. 17…”

Enantioselective Synthesis of Axially Chiral Sulfone-Containing Styrenes Based on Ion-Exchange Strategy

“…Sulfone-containing atropisomeric styrenes, which integrate the characteristics of axial chiral stilbene and sulfonyl species, have opened up new opportunities in the fields of organic synthesis and medicinal chemistry. − In 2018, Yan and co-workers reported the first organocatalytic synthesis of enantiomeric atropisomers of styrenes containing sulfonyl groups using sodium arylsulfinates as sulfur sources in the presence of proline and boric acid (Scheme A). Subsequently, they employed PhSO 2 H and α-amido sulfones as sulfur sources, constructing a series of novel sulfonyl-containing axially chiral styrenes based on the vinylidene ortho-quinone methide (VQM) intermediate .…”

“…In this reaction, the sulfur source is a sulfonyl radical generated in situ from a radical precursor and sulfur dioxide surrogates . Recently, Zhao’s research group has developed a sulfonylation strategy using β-sulfinyl esters as organosulfur reagents, which enables the in situ generation of sulfonyl anions through a redox transformation (Scheme B).…”