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Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 517-535

New regio-, stereo-, diastereo- and enantioselective one-pot reactions mediated by organometallic derivatives

Nicka Chinkov, G. Sklute, Helena Chechik, Adi Abramovitch, Deborah Amsallem, J. Varghese, Swapan Majumdar and I. Marek

Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel

Abstract: In the first part of the lecture, we will discuss the one-pot preparation of chiral homoallylic alcohol and amine derivatives by a copper-catalyzed four-component reaction. In this process, three new carbon-carbon bonds as well as a quaternary and a tertiary chiral center are created with excellent regio- and diastereoselectivities. When the reaction was performed without adding external electrophiles, a β-elimination reaction took place to give polysubstituted allenes in good overall yields. This strategy of zinc-homologation followed by a β-elimination reaction was also synthetically used for the transformation of sp3 sulfoxides into olefins with potential application in asymmetric synthesis. Finally, in the second part of this lecture, the stereoselective preparation of metallated dienes in only two chemical steps from commercially available products will be described. This new strategy is based on a tandem allylic C-H bond activation of a remote ω-double bond followed by an elimination reaction.