Overman rearrangement
From Infogalactic: the planetary knowledge core
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 requires heating but can also be catalyzed by Hg(II), or Pd(II) salts.[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
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- ↑ Organic Syntheses, Coll. Vol. 6, p.507; Vol. 58, p.4 (Article)
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Overman, L. E.; Carpenter, N. E. Org. React. 2005, 66, 1. doi:10.1002/0471264180.or066.01
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412–12413. (doi:10.1021/ja037086r)
- ↑ Asymmetric Overman Rearrangement Organic Syntheses, Vol. 82, p.134 (2005). (Article)
Further reading
- Isobe, M. et al. Tetrahedron Lett. 1990, 31, 3327.
- Allmendinger, T. et al. Tetrahedron Letters 1990, 31, 7301.
- Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M.; J. Org. Chem. 1998, 63(1), 188-192. PMID 11674062
