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A Soft Vinyl Enolization Approach to α-Acylvinyl Anions: Direct Aldol/Aldol Condensation Reactions of (E)-β-Chlorovinyl Ketones


  • This research was supported by IUPUI through a Research Support Fund Grant (2011 RSFG). We thank Dr. Karl Dria for his assistance with mass spectra analysis (CHE-0821661). The Bruker 500 MHz NMR was purchased through an NSF-MRI award (CHE-0619254).


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Synthesizing the synthons: The development of α-acylvinyl anion synthons has been achieved using direct α-vinyl enolization of α,β-unsaturated ketones under mild reaction conditions. The synthetic utility of such synthons has been demonstrated in intermolecular aldol and aldol condensation reactions, which provide synthetically useful allenyl ketone and enyne derivatives.

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