Highly Active Catalyst for Rearrangement

Highly Active Catalyst for Rearrangement

Author: Angewandte Chemie International Edition

The asymmetric counteranion-directed catalysis (ACDC) concept has been extended and exploited by Benjamin List and co-workers, Max Planck Institute for Coal Research, Mülheim an der Ruhr, Germany. A simple combination of commercially available reagents was used to design a catalyst capable of delivering good ee values with high yields in the Overman rearrangement of allylic imidates. The chiral TRIP counteranion combined with a simple commercially available palladacycle gave the palladium complex shown in the scheme below.

The observed enantioselectivity — and reaction mechanism — is explained in a qualitative manner based on the X-ray structure of the proposed ion-pair catalyst.

Overman rearrangement catalyst for Overman rearrangement

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