Overman rearrangement
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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]
See also
References
Further reading
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- ↑ Organic Syntheses, Coll. Vol. 6, p.507; Vol. 58, p.4 (Article Template:Webarchive)
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- ↑ Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412–12413. (Script error: No such module "doi".)
- ↑ Asymmetric Overman Rearrangement Organic Syntheses, Vol. 82, p.134 (2005). (Article Template:Webarchive)