Cooperative Lewis Acids and Aminocatalysis

This chapter describes the cooperative strategy of combining metal catalyst activation with aminocatalysis, with a focus on the metal acting as a Lewis acid catalyst. It gives examples where the metal catalyst promotes the reactivity of different substrates by the formation of reactive intermediates. These intermediates can act either as electrophiles or nucleophiles, which in turn can couple with nucleophilic enamine or electrophilic iminium intermediates formed between the carbonyl compounds and aminocatalyst. The chemical transformation ensues via the merging of the enamine and π‐allyl‐Pd complex via asymmetric counteranion‐direct catalysis (ACDC). Subsequently, several groups reported different co‐catalytic systems and chemical strategies for the α‐allylic alkylation of aldehydes and ketones. Cordova and coworkers reported the first example where iminium activation catalysis is combined with metal catalyst activation cooperatively. The stratagem was demonstrated for the catalytic enantioselective conjugate silyl addition to α,β‐unsaturated aldehydes.

Cordova, Armando,1970-Mittuniversitetet,Avdelningen för naturvetenskap(Swepub:miun)armcor (author)
MittuniversitetetAvdelningen för naturvetenskap (creator_code:org_t)

In:Chiral Lewis Acids in Organic SynthesisWeinheim, Germany : Wiley-Blackwell, s. 345-374

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