Synthesis of Stannyl‐Substituted d‐Glucal Derivatives via Palladium‐Catalyzed Regioselective Hydrostannation and Their Synthetic Applications
ChemistrySelect, 2016•Wiley Online Library
Stannyl derivatives of 2‐alkenyl acetylated D‐glucals have been synthesized via palladium‐
catalyzed regioselective hydrostannation in good yields under mild reaction conditions.
Factors affecting the regioselectivity of hydrostannation including chelation by the
neighbouring acetyl‐oxygen and the electronic effect of the substituent R on alkyne have
been evaluated. The synthetic applications of these stannyl derivatives of D‐glucal are
shown by performing Stille and Sonogashira cross‐coupling reactions to obtain a library of …
catalyzed regioselective hydrostannation in good yields under mild reaction conditions.
Factors affecting the regioselectivity of hydrostannation including chelation by the
neighbouring acetyl‐oxygen and the electronic effect of the substituent R on alkyne have
been evaluated. The synthetic applications of these stannyl derivatives of D‐glucal are
shown by performing Stille and Sonogashira cross‐coupling reactions to obtain a library of …
Abstract
Stannyl derivatives of 2‐alkenyl acetylated D‐glucals have been synthesized via palladium‐catalyzed regioselective hydrostannation in good yields under mild reaction conditions. Factors affecting the regioselectivity of hydrostannation including chelation by the neighbouring acetyl‐oxygen and the electronic effect of the substituent R on alkyne have been evaluated. The synthetic applications of these stannyl derivatives of D‐glucal are shown by performing Stille and Sonogashira cross‐coupling reactions to obtain a library of substituted 2‐alkenyl derivatives of D‐glucal.
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