Overman rearrangement

The Overman rearrangement is a chemical reaction that can be described as a Claisen rearrangement of allylic alcohols to give allylic trichloroacetamides through an imidate intermediate.^[1]^[2]^[3] The Overman rearrangement was discovered in 1974 by Larry Overman.^[4]

The [3,3]-sigmatropic rearrangement is diastereoselective and requires heating or the use of Hg(II) or Pd(II) salts as catalysts.^[5] The resulting allylamine structures can be transformed into many chemically and biologically important natural and un-natural amino acids (like (1-adamantyl)glycine).^[6]

The Overman rearrangement may also be used for asymmetric synthesis.^[7]^[8]

References

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^ Organic Syntheses, Coll. Vol. 6, p.507; Vol. 58, p.4 (Article Archived 2011-05-14 at the Wayback Machine)
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^ Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412–12413. (Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).)
^ Asymmetric Overman Rearrangement Organic Syntheses, Vol. 82, p.134 (2005). (Article Archived 2011-05-14 at the Wayback Machine)