Formation of a carbon–palladium bond to the unsubstituted cyclopentadiene ring occurs during the cyclopalladation of 4‐ferrocenyl‐1,3‐oxazolines and leads to a new type of metalated ferrocene (see scheme). These chiral complexes catalyze the asymmetric aza‐Claisen rearrangement of allylic imidates.
The synthesis of nicotine with enantiomeric excess of >99% ee was accomplished by asymmetric Ir-catalysed allylic amination followed by ring closing metathesis and racemization-free double bond reduction.
The Sharpless asymmetric dihydroxylation (AD) of 1-substituted-1-ferrocenylethenes takes place with good yields and with moderate to good enantioselectivities. The resulting 1-substituted-1-ferrocenyl-1,2-ethanediols are the first alpha-chiral tertiary ferrocenylcarbinols that have been prepared in optically active form. Their absolute configuration, ascertained by Induced Circular Dichroism (ICD), shows that in all cases the ferrocenyl moiety has the highest affinity for the SW binding pocket of the AD ligands. Depending upon the reaction conditions, significant racemization takes place during a side-chain azide nucleophilic substitution on 2-ferrocenyl-1,2-propanediol.
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