A metal-free Petasis reaction towards the synthesis of N-(α-substituted)alkyl sulfoximines/sulfonimidamides

Herein, we disclose a metal-free novel approach for the synthesis of N-(α-substituted)alkyl sulfoximines/sulfonimidamides via one-pot multicomponent Petasis reactions of aryl boronic acids, ortho-hydroxyarylaldehydes and sulfoximines/sulfonimidamides in moderate to very good yields. The presence of...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-08, Vol.19 (32), p.7061-7065
Hauptverfasser: Natarajan, K, Irfana Jesin, C P, Antony Haritha Mercy, A, Nandi, Ganesh Chandra
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Sprache:eng
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Zusammenfassung:Herein, we disclose a metal-free novel approach for the synthesis of N-(α-substituted)alkyl sulfoximines/sulfonimidamides via one-pot multicomponent Petasis reactions of aryl boronic acids, ortho-hydroxyarylaldehydes and sulfoximines/sulfonimidamides in moderate to very good yields. The presence of two chiral centres provides a mixture of diastereomers almost in a 1 : 1 ratio, which are separated successfully in most of the cases. The -OH functionality of Petasis products is further utilized to derive heterocycles via O-allylation, followed by intramolecular Heck cyclization, proving the synthetic utility of the products.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01181b