Abstract
Abstract A palladium-catalyzed asymmetric bis(alkoxycarbonylation) reaction of 1,2-dihydronaphthalenes and related cyclic olefins in the presence of copper(I) triflate was achieved by using a chiral bioxazoline ligand under normal pressure of carbon monoxide and oxygen to give the corresponding optically active cis-dicarboxylates with enantioselectivities up to 94% ee. An asymmetric intra- and intermolecular bis(alkoxycarbonylation) reaction of a prochiral diol possessing dihydronaphthalene skeleton also proceeded enantioselectively by an appropriate selection of the substituent of bioxazoline ligand. The carbonylation product derived from 8-methoxy-1,2-dihydronaphthalene was applied to the synthesis of a biologically active hexahydrobenz[e]isoindole derivative.
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