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The Voight reaction on tertiary α-hydroxy ketones.
- Source :
-
Tetrahedron . Nov2015, Vol. 71 Issue 44, p8391-8406. 16p. - Publication Year :
- 2015
-
Abstract
- The Voight reaction is for the transformation of secondary α-hydroxy ketones into corresponding α-amino ketones. Although discovered as early as 1886, it has not enjoyed wide popularity in organic synthesis, as it is applicable to only secondary α-hydroxy ketones. In terms of extending the applications of the reaction, we have shown that the reaction takes place on tert -α-hydroxy ketones also, particularly when present on rigid planar molecular frameworks like phenanthrene, pyrene and acenaphthylene. The reaction is not a simple substitution of the hydroxy group with amines, but goes through imine formation followed by 1,2-C migration. The reaction provides good opportunity for the synthesis of optically active α-amino ketones. We have achieved facile synthesis of some chromatographically separable and optically active tert -α-amino ketones by employing S -(−) or R -(+)-α-methylbenzylamines in the Voight amination. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 71
- Issue :
- 44
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 110007796
- Full Text :
- https://doi.org/10.1016/j.tet.2015.08.069