A convergent method for the synthesis of highly substituted pyridines will be discussed. Vinylallenes (synthesized by a variety of methods) react with tosyl cyanide in a tandem [4+2] cycloaddition/ base induced isomerization process to give sulfonyl pyridines. These pyridines participate in substitution reactions with nucleophiles leading to a variety of alkyl, alkenyl, aryl, and alkoxy derivatives. This talk will focus on the mechanism, scope, and limitations of this new strategy.

Convergent Diels-Alder strategy for the synthesis of highly substituted pyridines

256th National Meeting (2018)

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