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Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes

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posted on 2016-02-22, 17:11 authored by Jennifer Tsoung, Katja Krämer, Adam Zajdlik, Clemence Liébert, Mark Lautens
An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intramolecular Friedel–Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.