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Combining NHC–Cu and Brønsted Base Catalysis: Enantioselective Allylic Substitution/Conjugate Additions with Alkynylaluminum Reagents and Stereospecific Isomerization of the Products to Trisubstituted Allenes

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  • Financial support was provided by the NIH (GM-47480); J.A.D. is grateful for a LaMattina Graduate Fellowship. We thank Boston College Research Services for providing access to computational facilities and G. Talavera and S. M. Couvertier for experimental assistance. NHC=N-heterocyclic carbene.

Abstract

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All-catalytic route to trisubstituted allenes: The first examples of catalytic enantioselective allylic substitution reactions that involve alkyne-based nucleophiles and lead to products having tertiary stereogenic centers are followed by an exceptionally stereospecific amine-catalyzed isomerization to trisubstituted allenes (see picture; NHC=N-heterocyclic carbene).

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