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Overman Rearrangement
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Abstract
The thermal or Hg(II) or Pd(II) promoted rearrangement of an allyl trichloroacetimidate into an allyl trichloroacetamide is generally known as the Overman rearrangement. This rearrangement is generally carried out in a dry and nonnucleophilic solvent to minimize the hydrolysis of allyl trichloroacetimidate. It has been found that the substitution of potassium hydride with a catalytic amount of DBU improves the yield. In addition, this rearrangement is difficult for the unsaturated pyranose substrates with axial hydroxy groups at the 1 and 4 positions. This reaction is useful in organic synthesis for the preparation of a variety of nitrogen‐containing compounds especially for the preparation of the sterically hindered allylic amines that are difficult to obtain from conventional methods.
Title: Overman Rearrangement
Description:
Abstract
The thermal or Hg(II) or Pd(II) promoted rearrangement of an allyl trichloroacetimidate into an allyl trichloroacetamide is generally known as the Overman rearrangement.
This rearrangement is generally carried out in a dry and nonnucleophilic solvent to minimize the hydrolysis of allyl trichloroacetimidate.
It has been found that the substitution of potassium hydride with a catalytic amount of DBU improves the yield.
In addition, this rearrangement is difficult for the unsaturated pyranose substrates with axial hydroxy groups at the 1 and 4 positions.
This reaction is useful in organic synthesis for the preparation of a variety of nitrogen‐containing compounds especially for the preparation of the sterically hindered allylic amines that are difficult to obtain from conventional methods.
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