Issue 16, 2023

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 disclosed to generate sulfinate anions. Based on this strategy, the asymmetric sulfonylation of vinylidene o-quinone methides has been achieved, providing various sulfone-based axially chiral styrenes in excellent enantioselectivities.

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

Supplementary files

Article information

Article type
Research Article
Submitted
20 Haz 2023
Accepted
30 Haz 2023
First published
03 Tem 2023

Org. Chem. Front., 2023,10, 3975-3981

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

S. Xiang, T. Lu, J. Liu and Q. Zhao, Org. Chem. Front., 2023, 10, 3975 DOI: 10.1039/D3QO00932G

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