Enantioselective Addition of Dialkyl Malonates to β‑Arylethenesulfonyl Fluorides under High-Pressure Conditions

Enantioselective Addition of Dialkyl Malonates to β‑Arylethenesulfonyl Fluorides under High-Pressure Conditions

Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yields of up to 96% an...

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Veröffentlicht in:Organic letters 2023-09, Vol.25 (37), p.6818-6822
Hauptverfasser: Kopyt, Michał, Tryniszewski, Michał, Barbasiewicz, Michał, Kwiatkowski, Piotr
Format: Artikel
Sprache:eng
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Zusammenfassung:Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yields of up to 96% and enantioselectivities of up to 92%. Functionalization of the adducts via sulfur fluoride exchange (SuFEx) reaction and desulfonylative cyclization is demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02302