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| The ] is a ] that can be described as a ] of ] alcohols to give allylic trichloroacetamides. The Overman rearrangement was discovered in ] by ]. | The ] is a ] that can be described as a ] of ] alcohols to give allylic trichloroacetamides. The Overman rearrangement was discovered in ] by ]. | ||
| ] | ] | ||
| The -sigmatropic rearrangement]] is ] and can be catalyzed by heat, ], or ]. The resulting allylamine structures can be transformed into many chemically and biologically important natural and un-natural amino acids.<ref>{{cite journal | last=Chen | first=Y. K. | coauthors=Lurain, A. E.; Walsh, P. J. | title=A General, Highly Enantioselective Method for the Synthesis of <small>D</small> and <small>L</small> ά-Amino Acids and Allylic Amines | journal=J. Am. Chem. Soc. | year=2002 | volume=124 | pages=12225–12231 }}</ref |
The -sigmatropic rearrangement]] is ] and can be catalyzed by heat, ], or ]. The resulting allylamine structures can be transformed into many chemically and biologically important natural and un-natural amino acids.<ref>{{cite journal | last=Chen | first=Y. K. | coauthors=Lurain, A. E.; Walsh, P. J. | title=A General, Highly Enantioselective Method for the Synthesis of <small>D</small> and <small>L</small> ά-Amino Acids and Allylic Amines | journal=J. Am. Chem. Soc. | year=2002 | volume=124 | pages=12225–12231 }}</ref> | ||
Revision as of 06:39, 26 April 2007
The Overman rearrangement is a chemical reaction that can be described as a Claisen rearrangement of allylic alcohols to give allylic trichloroacetamides. The Overman rearrangement was discovered in 1974 by Larry Overman.
The -sigmatropic rearrangement is diastereoselective and can be catalyzed by heat, Hg(II), or Pd(II). The resulting allylamine structures can be transformed into many chemically and biologically important natural and un-natural amino acids.
References
- Chen, Y. K. (2002). "A General, Highly Enantioselective Method for the Synthesis of D and L ά-Amino Acids and Allylic Amines". J. Am. Chem. Soc. 124: 12225–12231.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help)
- Overman, L. E. J. Am. Chem. Soc. 1974, 96, 597.
- Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
- Overman, L. E. Accts. Chem. Res. 1980, 13, 218-224. (Review)
- Organic Syntheses, Coll. Vol. 6, p.507; Vol. 58, p.4 (Article)
- Isobe, M. et al. Tetrahedron Lett. 1990, 31, 3327.
- Allmendinger, T. et al. Tetrahedron Lett. 1990, 31, 7301.
- Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M.; J. Org. Chem. 1998, 63(1), 188-192. (PMID: 11674062)
- Asymmetric Overman Rearrangement Organic Syntheses, Vol. 82, p.134 (2005). (Article)