Asymmetric Epoxidation
Using Iminium Salt Organocatalysts Featuring Dynamically Controlled
Atropoisomerism
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Abstract
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