Cycloaromatization processes have proved to be efficient approaches for the synthesis of molecules in high complexity. Recently we discovered a mild base-mediated, [4 + 2] net cycloisomerization of substrates having motif 1, which produces reactive intermediates that we presume to be derivatives of a,3-dehydrotoluene (cf. 2, species previously formed only by Myers-Saito electrocyclization reaction of allenyl enynes). We call this process the pentadehydro-Diels-Alder (PDDA) reaction. Trapping of this intermediate leads to various isoindoline derivatives 3 by means of in situ trapping reactions. We will also present our studies toward understanding the mechanism of this novel transformation.

Pentadehydro-Diels-Alder (PDDA) reaction.Part 1: Cycloisomerization of triynes to a,3-dehydrotoluene derivatives and their trapping reactions

249th National Meeting (2015)

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