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Abstract Functionalized diazo hydroxylamines are prepared by an efficient Mukaiyama-Mannich addition of α-diazo silyl enolate with nitrones under mild reaction conditions. This protocol provides a variety of 1,2-addition adducts in… Click to show full abstract
Abstract Functionalized diazo hydroxylamines are prepared by an efficient Mukaiyama-Mannich addition of α-diazo silyl enolate with nitrones under mild reaction conditions. This protocol provides a variety of 1,2-addition adducts in good to excellent yields, which are potentially of great importance in medicinal chemistry. MgI2 etherate (MgI2·(OEt2)n) is the preferred catalyst and this addition proceeds without decomposition of the diazo moiety. Furthermore, this MgI2·(OEt2)n catalyzed reaction shows unique chemoselectivity towards nitrones with aldehydes or aldimines.
Journal Title: Tetrahedron
Year Published: 2020
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