Journal
ACS CATALYSIS
Volume 12, Issue 15, Pages 9806-9811Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c02691
Keywords
cobalt; sulfur-stereogenic sulfoximines; asymmetric C-H activation; chiral carboxylic acid; N,S-chiral sulfoxide ligands
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Funding
- NSFC [21925109, 21801223]
- Zhejiang Provincial NSFC [LD22B030003]
- National Key R&D Program of China [2021YFF0701600]
- Fundamental Research Funds for the Central Universities [226-2022-00224, 226-2022-00175]
- Open Research Fund of School Chemistry and Chemical Engineering, Henan Normal University
- Center of Chemistry for Frontier Technologies of Zhejiang University
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In this study, we report the synthesis of sulfur-stereogenic sulfoximines through Co(III)/chiral carboxylic acid-catalyzed reaction. The synthetic yields and enantioselectivities are high, and the products can be further transformed into recyclable chiral auxiliaries.
Sulfoximines bearing stereogenic sulfur atoms are ubiquitous motifs in pharmaceuticals, agricultural chemicals, and bioactive compounds. Herein, we report the synthesis of sulfur-stereogenic sulfoximines via Co(III)/chiral carboxylic acid-catalyzed enantioselective C-H amidation. A broad range of cyclic and acyclic sulfur-stereogenic sulfoximines were isolated in good yields and enantioselectivities (up to an 86% yield and 1.5:98.5 er). The acyclic amidation products can be reduced to potential N,S-chiral sulfoxide ligands, which could be further transformed into recyclable chiral auxiliaries in the Pd-catalyzed diastereoselective C(sp(3))-H activation of aliphatic carboxylic acids.
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