Dinuclear Zinc-Catalyzed Asymmetric Tandem Reaction of α-Hydroxy-1-indanone: Access to Spiro[1-indanone-5,2′-γ-ybutyrolactones]

A highly efficient method for the enantioselective build of spiro[1-indanone-5,2'-gamma-butyrolactones] has been developed through the tandem Michael/transesterification reaction of alpha-hydroxy-l-indanone and alpha,beta-unsaturated esters. A broad range of spiro(1-indanone-butyrolacones) with contiguous stereocenters have been synthesized with excellent stereoselectivities (up to >20:1 dr, up to >99% ee) under the catalysis of dinuclear zinc complex. Moreover, the reaction can be run on a gram scale without affecting its stereoselectivities. A possible mechanism is proposed.