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Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines.
Enantioselective symmetrising–desymmetrising allylic oxidation of racemic bridged bicyclic alkenes using an asymmetric copper-catalysed Kharasch–Sosnovsky reaction has been explored. Good yields and reasonable levels of induction (up to 70% ee) have been obtained using carbocyclic systems as substrates.
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