caa a22 4500 37892320X CHVBK 20180305123610.0 cr unu---uuuuu 161128e20040101xx s 000 0 eng 10.1351/pac200476030517 doi (NATIONALLICENCE)gruyter-10.1351/pac200476030517 New regio-, stereo-, diastereo- and enantioselective one-pot reactions mediated by organometallic derivatives [Elektronische Daten] [Nicka Chinkov, G. Sklute, Helena Chechik, Adi Abramovitch, Deborah Amsallem, J. Varghese, Swapan Majumdar, I. Marek] 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. © 2013 Walter de Gruyter GmbH, Berlin/Boston Chinkov Nicka Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Sklute G. Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Chechik Helena Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Abramovitch Adi Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Amsallem Deborah Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Varghese J. Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Majumdar Swapan Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Marek I. Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut Pure and Applied Chemistry De Gruyter 76/3(2004-01-01), 517-535 0033-4545 76:3<517 2004 76 pac https://doi.org/10.1351/pac200476030517 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1351/pac200476030517 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Chinkov Nicka Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 700 1- Sklute G. Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 700 1- Chechik Helena Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 700 1- Abramovitch Adi Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 700 1- Amsallem Deborah Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 700 1- Varghese J. Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 700 1- Majumdar Swapan Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 700 1- Marek I. Department of Chemistry and Institute of Catalysis Science and Technology - Technion-Israel Institute of Technology, Technion City 32000 Haifa, Israel aut NATIONALLICENCE 773 0- Pure and Applied Chemistry De Gruyter 76/3(2004-01-01), 517-535 0033-4545 76:3<517 2004 76 pac CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter