A regioselective synthesis of 3-chloro-3-deoxy sugars by dichlorobis(benzonitrile)palladium(II)

A Ratiometric Fluorescent Probe for Biological Signaling Molecule H2S: Fast Response and High Selectivity

“…Voelter and co‐workers reported the regioselective synthesis of 3‐chloro‐3‐deoxy sugars from 2,3‐anhydro sugars and over‐stoichiometric amounts of PdCl 2 (PhCN) 2 [Equation (38)] in 1983 63. According to 1 H NMR spectroscopy, the substrates shown in Equation (38) exist almost entirely in the conformations depicted in Schemes and .…”

Pd‐Mediated Reactions of Epoxides

“…[88] Saegusa et al observed that these isomerizations can occur at lower reaction temperature and with higher rates in the presence of benzoylacetic acid [Equation (63)]. [91,98] Saegusa's reactions, however, were carried out with larger amounts of catalyst [Equation (63)] and the isomerization pathway involved only a few substrates. Indeed, 3,4-epoxybut-1-ene and 4,5-epoxyhex-2-ene were benzoylated under these conditions, providing keto allylic alcohols [Equation (64)].…”

“…[63] According to 1 H NMR spectroscopy, the substrates shown in Equation (38) exist almost entirely in the conformations depicted in Schemes 10 and 11. The reactions presumably occur through the coordination of the oxirane oxygen to palladium and the simultaneous trans attack of a chloride atom belonging to another molecule of the complex.…”

Stereodefined Access to 3‐Deoxy Sugars Through a Tandem Baylis–Hillman and Lewis Acid Catalyzed Reaction Sequence

“…[8] These drawbacks can be overcome by total synthesis approaches using flexible methodologies that allow a high degree of stereoselection. [8] Classical synthesis of 3-deoxy sugars bank either on the deoxygenation strategy [11] or β-elimination followed by catalytic hydrogenation protocol. [12] Herein we report an innovative synthesis of 3-deoxy sugars 9 and 10 in both  and …”