Multi-component cycloaddition approaches in the catalytic asymmetric synthesis of alkaloid targets
- 15 September 2009
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 38 (11), 3149-3159
- https://doi.org/10.1039/b816702h
Abstract
Cycloaddition reactions are attractive strategies for the rapid formation of molecular complexity in organic synthesis, as multiple bonds are formed in a single process. To this end, several research groups have been actively involved in the development of catalytic methods to activate readily accessible π-components to achieve cycloadditions. However, the use of C–N π-components for the formation of heterocycles by these processes is less well developed. It has been previously demonstrated that the combination of different isocyanates with two alkynes yields pyridones of several types by metal-catalyzed [2 + 2 + 2] cycloadditions. The potential of this chemistry has been extended to alkenes as C–C π-components, allowing the formation of sp3-stereocenters. In this tutorial review directed towards [n + 2 + 2] cycloadditions of heterocumulenes, alkynes and alkenes, the recent advances in the catalytic asymmetric synthesis of indolizidine, quinolizidine and azocine skeletons are discussed.Keywords
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