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In this paper we report our studies on 6-endo- versus 5-exo-trig cyclizations of 2-heteroyl-1-methylene-1,2,3,4-tetrahydroisoquinolines. This can be used for the construction of a variety of functionalized five- or six-membered heterocyclic rings.
Chiral (Z-enol ethers 7a-7p have been prepared in two steps. Bradsher cycloaddition between such compounds and 2,7-naphthyridinium salt 4b in water or in ter-butanol-water afforded, in some cases with good yield and diastereoselectivity, highly functionalized isoquinoline derivatives, potential intermediates in Manzamine A 1 total synthesis. X-Ray analysis secured the direction of asymmetric induction...