7 research outputs found
Carbohydrate-derived iminium salt organocatalysts for the asymmetric epoxidation of alkenes
A new family of carbohydrate-based dihydroisoquinolinium salts has been prepared and tested for potential as asymmetric catalysts for the epoxidation of unfunctionalized alkene substrates, providing up to 57% ee in the product epoxides
Activation of hydrogen peroxide by diphenyl diselenide for highly enantioselective oxaziridinium salt mediated catalytic asymmetric epoxidation
The first reported use of benzeneperseleninic acid as a catalytic mediator for oxaziridinium ion catalysed epoxidation is described, providing reaction rates and ee values (up to 85%) similar to those reported when using oxone as the stoichiometric oxidant. A dual catalytic cycle is proposed, in which diphenyl diselenide is initially converted into the perseleninic acid, which in turn oxidises an iminium ion to the corresponding oxaziridinium species, thus facilitating asymmetric oxygen transfer to an alkene. Ā© Georg Thieme Verlag
Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation
We report the first enantioselective total synthesis
of (+)-scuteflorin
A in 14% overall yield, employing a chiral iminium salt to effect
an organocatalytic asymmetric epoxidation of xanthyletin in >99%
ee
as the key step
Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation
We report the first enantioselective total synthesis
of (+)-scuteflorin
A in 14% overall yield, employing a chiral iminium salt to effect
an organocatalytic asymmetric epoxidation of xanthyletin in >99%
ee
as the key step
Kinetic Resolution in Asymmetric Epoxidation using Iminium Salt Catalysis
The
first reported examples of kinetic resolution in epoxidation
reactions using iminium salt catalysis are described, providing up
to 99% ee in the epoxidation of racemic <i>cis</i>-chromenes
Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring Dynamically Controlled Atropoisomerism
Introduction of a pseudoaxial substituent at a stereogenic
center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived
azepinium salt organocatalysts affords improved enantioselectivities
and yields in the epoxidation of unfunctionalized alkenes. In the
biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis
is controlled by the interaction of this substituent with the chiral
substituent at nitrogen
Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring Dynamically Controlled Atropoisomerism
Introduction of a pseudoaxial substituent at a stereogenic
center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived
azepinium salt organocatalysts affords improved enantioselectivities
and yields in the epoxidation of unfunctionalized alkenes. In the
biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis
is controlled by the interaction of this substituent with the chiral
substituent at nitrogen