Topologically driven tandem radical cyclization-based strategy for the synthesis of oxa- and aza-cages |
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Authors: | Santosh J Gharpure Suheel K Porwal |
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Institution: | Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India |
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Abstract: | Tandem radical cyclization-based strategy for the synthesis of oxa- and aza-cage compounds is described. The aryl iodides 1 and N-tosyl propargylated amine 8 lead to oxa- and aza-cages, respectively, after two tandem 5-exo-trig radical cyclizations. The alcohols 11 on reaction with nBu3SnH and AIBN give rise to the oxa-cages 14 bearing the tributyltin moiety after three tandem 5-exo-trig cyclizations. On the other hand, reaction of the propargyl ether 16 under similar conditions furnishes the oxa-cage 17 by a 5-exo-trig, 4-exo-trig, 5-exo-trig tandem radical cyclization sequence. |
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Keywords: | Tandem reactions Oxa-cages Aza-cages Radical cyclization |
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