Search Thermo Fisher Scientific
Overman Rearrangement
In 1974, the American chemist Larry Overman reported the thermal and mercuric ion catalyzed rearrangement of allylic trichloroacetimidates to create the corresponding trichloroacetamides. Subsequently the 1,3-transposition of alcohol and amine functionalities via [3,3]-sigmatropic rearrangement of allylic trichloroacetimidates became known as the Overman rearrangement. The allylic trichloroacetimidates are readily prepared by treating the corresponding alcohols with trichloroacetonitrile in the presence of catalytic amounts of a base, or DBU.
In recent decades, the Overman rearrangement has become an important carbon-nitrogen bond-forming reaction used in many synthesis campaigns. For example, during the total synthesis of sphingofungin E by N. Chida and colleagues, the stereocenter at C5 was formed using the Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose.
Mechanism of the Overman rearrangement reaction
Click image to enlarge
Review available Thermo Scientific products for the Overman rearrangement reaction:
Vote for your favorite named reaction
Learn more about the most popular named reactions in chemistry based on feedback from our customers. Do you have a favorite reaction? Let us know!
Resources
Support
For Research Use Only. Not for use in diagnostic or therapeutic procedures.