Enantioselective Addition of Boronates to Acyl Imines Catalyzed by Chiral Biphenols

Joshua A. Bishop, Sha Lou, Scott E. Schaus

Angewandte Chemie International Edition · 2009 · 78 citations · 41 references

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Abstract

On the big screen: A chiral biphenol catalyst screening protocol was developed for the rapid identification of enantioselective nucleophilic boronate reactions with acyl imines (see scheme). The approach successfully identified a unique catalyst for the reaction of aryl, vinyl, and alkynyl boronates. Mechanistic studies demonstrate boronate ligand exchange with the catalyst is necessary for activation towards nucleophilic addition.

References

41