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Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluor­enyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines

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The discovery and development of an Ir-catalyzed asymmetric umpolung allylation of imines is discussed here. This method produces 1,4-disubstituted homoallylic amines, a class of compounds that are difficult to access… Click to show full abstract

The discovery and development of an Ir-catalyzed asymmetric umpolung allylation of imines is discussed here. This method produces 1,4-disubstituted homoallylic amines, a class of compounds that are difficult to access by conventional methods. This reaction proceeds through a sequence involving an allylation and a 2-aza-Cope rearrangement event. The unique mechanistic feature of this reaction could be the reason for its broad substrate scope. The products of this reaction are useful intermediates for various bioactive and natural products. Besides its immediate synthetic utility, we expect this transformation to inspire the development of other umpolung functionalizations of imines and Ir-catalyzed asymmetric allylic substitution (AAS) reactions. 1 Introduction 2 Reaction Discovery 3 Substrate Scope 4 Conclusion

Keywords: catalyzed asymmetric; homoallylic amines; umpolung allylation; asymmetric umpolung; disubstituted homoallylic; allylation

Journal Title: Synlett
Year Published: 2017

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