A formal homo-Nazarov cyclization of enantioenriched donor–acceptor cyclopropanes and following transformations: asymmetric synthesis of multi-substituted dihydronaphthalenes

Abstract

Multi-substituted trans-dihydronaphthalenes were obtained in high enantiomeric excess from a TiCl₄-mediated cyclization of enantioenriched donor–acceptor cyclopropanes, followed by a triflation of the hydroxy groups. The C–OTf bond in these multi-substituted trans-dihydronaphthalenes is susceptible to further Pd-catalyzed hydrogenations and coupling reactions, which afforded the corresponding C–H or C–C bonded products.