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| - On the Mechanism of Oxazoline-Directed Metalations: Evidencefor Nitrogen-Directed Reactions
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| - We recently described a method for the synthesis of ferrocenecomplexes possessing planar chiralitywhich relies on the asymmetric deprotonation of chiralferrocenyloxazolines. The unexpectedstereochemical outcome of these reactions led us to examine whether themetalation is directed bythe oxygen or the nitrogen of the oxazoline. In this paper, wedescribe the synthesis of a constrainedferrocenyloxazoline (compound 13) in which oxygen- andnitrogen-directed metalations providedifferent stereochemical outcomes. Our results show that nitrogenis responsible for the directiveeffects of the oxazoline when alkyllithium reagents are used todeprotonate the ferrocene. Theimplications of this result on the origin of asymmetric induction inthe metalation of theunconstrained ferrocenyloxazolines 19 and 20 arediscussed.
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