American Chemical Society
ja051526s_si_001.pdf (2 MB)

Direct Asymmetric Zn−Aldol Reaction of Methyl Vinyl Ketone and Its Synthetic Applications

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journal contribution
posted on 2005-06-22, 00:00 authored by Barry M. Trost, Seunghoon Shin, Joseph A. Sclafani
A direct catalytic asymmetric aldol reaction of methyl vinyl ketone is described using our dinuclear zinc catalyst. The obtained aldol adduct functions as a bifunctional building block by utilization of the vinyl functionality. For example, convergent fragment coupling methods have been demonstrated via highly diastereoselective cycloaddition of nitrile oxide after reduction into 1,3-diol or via cross-metathesis reaction.