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In 2007, we presented the application of an efficient regioand stereoselective Heck-Matsuda (HM) arylation of N-carbomethoxy-L-3-dehydroproline methyl ester (1) with arenediazonium tetrafluoroborates in the syntheses of aryl kainoids with potent neurotoxic activities. 2 Recently, new studies using arenediazonium salts containing EWG showed an unexpected inversion of the enantioselectivity in these substrate directable HM reactions. Herein we report the details of these investigations and a possible rationalization for this surprising result.

Substrate Directable Heck-Matsuda Reactions: Studies on the Synthesis of 4-Arylprolines