Our initial studies of the (4+3) cycloaddition reaction of oxidopyridinium ions showed that the reaction proceeded well in terms of yield and with high regioselectivity, but poor endo/exo selectivity. This result inspired our interest in developing a means to control the endo/exo selectivity of the process. We began with modifying the diene by introducing a bulky group at the 2-position, while maintain the substitution pattern that we knew afforded high regioselectivity. As expected, we obtained good endo selectivity and regioselectivity in reactions using 2-silylated dienes. This poster will describe the synthesis of the silylated dienes used in the study, the results of the (4+3) cycloaddition, and the rationalization of the outcome provided by computational analyses.

Endo selectivity in the (4+3) cycloaddition of oxidopyridinium ions

ACS Spring 2022

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