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

Nicka Chinkov, Genia Sklute, Helena Chechik, Adi Abramovitch, Deborah Amsallem, Jos Varghese, Swapan Majumdar, Ilan Marek

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Pages (from-to)517-535
Number of pages19
JournalPure and Applied Chemistry
Issue number3
StatePublished - Mar 2004
Externally publishedYes

Bibliographical note

Funding Information:
This research was supported by a grant from the G.I.F., the German-Israeli Foundation for Scientific Research and Development (I-693-7.5/2001), by the Israel Science Foundation administrated by the Israel Academy of Science and Humanities (79/01-1), and by the Fund for the Promotion of Research at the Technion.

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering


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