Stereoselective synthesis of seven-membered rings using intramolecular (4+3) cycloaddition reactions
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Heterocyclic molecules containing seven-membered rings have importance in organic synthesis owing to their presence in some natural products and biologically active molecules. Furthermore, these scaffolds act as important tools for developing new drugs and biological probes. A stereoselective, intramolecular (4+3) cycloaddition of an oxidopyridinium ion has been developed. N-Alkylation of a nicotinate derivative followed by reaction under basic condition in acetonitrile afforded (4+3) cycloaddition products in excellent yield and high stereoselectivity. Substitution at the 3, 2-TMS, and 1, 3 positions of the diene resulted in 100 [percent] stereoselectivity.
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