Abstract
In this review we have sought to give the reader an appreciation of the many synthetic applications now known for the more popular asymmetric (3,3)sigmatropic rearrangements. The ability to predict the stereochemical outcome of the rearrangements, and the ability to prepare products containing several contiguous chiral centres makes the application of such asymmetric rearrangements an attractive proposition to the synthetic chemist. We, and others, have begun to develop the amino-Cope rearrangement as a new synthetic protocol that appears to have much untapped potential. The question of the whether the rearrangement proceeds via a stepwise or concerted mechanism, and if the mechanistic pathway can be controlled, remains to be established. Current work in our group is aimed at applying the asymmetric amino-Cope rearrangement in synthetically useful procedures, for example in the synthesis of highly functionalised oxygen and nitrogen heterocycles. Our progress in this area will be reported in due course.
Keywords: Asymmetric, Sigmatropic, amino-Cope rearrangement, Asymmetric Ireland-Claisen Rearrangement, Aza Claisen Rearrangements
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
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