Abstract
The synthesis of new carbon-carbon and carbon-heteroatom bonds in a stereochemically well defined manner still presents a challenge in modern synthetic methodology. An important class of reactions, which can carry out the aforementioned transformations, are the [3,3]-sigmatropic rearrangements. These rearrangements have traditionally been carried out thermally at high temperatures. However, the discovery that these transformations can be accelerated by Pd(II) at ambient temperature has led to more widespread use of these reactions for the synthesis of biologically active and pharmaceutically important molecules. This review presents an overview of the use of palladium(II) catalysis for the acceleration of three of the most commonly used rearrangements in organic chemistry, namely, the Cope, Claisen and aza-Claisen rearrangements. In particular, the mechanism of catalysis, stereochemical outcome and synthetic application of these reactions will be discussed.
Keywords: Pd(II)-catalysed rearrangements, thermal Cope rearrangement, 1,5-hexadienes, Claisen rearrangement, N-(4-trifluorophenylbenzimidate, 3-aminodeoxystatine derivatives
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
8