Chan rearrangement

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The Chan rearrangement is a

acyloxy acetate (1) in the presence of a strong base to a 2-hydroxy-3-keto-ester (2).[1]

The Chan rearrangement
The Chan rearrangement

This procedure was employed in the Holton Taxol total synthesis.[2]

Reaction mechanism

The

oxirane
. Acidic workup liberates the free hydroxyl group.

The mechanism of the Chan rearrangement
The mechanism of the Chan rearrangement

References

  1. )
  2. )

See also