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N-Activated 2-phenylazetidines were opened regioselectively at the benzylic carbon with various allylsilanes or propargylsilane in the presence of BF 3 ·Et 2 O, providing amino olefins, precursors of biomolecules such as phenyl-homo-kainoids.
Two intramolecular routes were experimented to reach the hexahydrobenzofuro[2,3-c]pyridine platform: a Heck and a radical reaction. The radical route was applicable to all substrates, whereas the Heck route was of limited use. The key adducts were obtained via a Mitsunobu condensation between halogenated phenols and an allylic alcohol, the 3-hydroxy-tetrahydropyridine.
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