Consecutive carbon-carbon bond formation approach in tandem cyclization reactions.
The conventional tandem cyclization reactions involve the formation of alternating carbon-carbon bonds, whereas the newly developed cyclization reactions involve the formation of consecutive carbon-carbon bonds, in which N-aziridinylimines have been utilized as geminal radical acceptor and donor equivalents in a single operation. This unprecedented tandem cyclization approach becomes feasible by the successful generation of 5- and 6-membered ring radicals by radical cyclizations of N-aziridinylimines. The same notion can be applied to the anionic cyclizations of N-aziridinylimines, thereby allowing anionic consecutive carbon-carbon bond formation. This approach has great synthetic potential, particularly for the construction of quaternary carbon centers, and it provides highly efficient routes for the synthesis of natural products.
Kim
S
S
Center for Molecular Design and Synthesis and Department of Chemistry, School of Molecular Science, Korea Advanced Institute of Science and Technology, Taejon 305-701, Korea. skim@mail.kaist.ac.kr
D001388:Aziridines / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry
D001388:Aziridines; D001685:Biological Factors; D005609:Free Radicals; D006844:Hydrocarbons, Cyclic; D007097:Imines; C033132:aziridine