New regio-, stereo-, diastereo- and enantioselective one-pot reactions
mediated by organometallic derivatives
N. Chinkov, G. Sklute, H. Chechik, A. Abramovitch, D. Amsallem, J.
Varghese, S. 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 b-elimination reaction took place to give
polysubstituted allenes in good overall yields. This strategy of zinc-homologation
followed by a b-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 w-double
bond followed by an elimination reaction.
*Plenary and invited lectures presented at the 12th
International Symposium on Organometallic Chemistry Directed Towards
Organic Synthesis (OMCOS-12), Toronto, Ontario, Canada, 6-10 July 2003.
Other lectures are published in this issue, pp.
453-695.
Page last modified 20 May 2004.
Copyright © 2004 International Union of Pure and Applied Chemistry.
Questions or comments about IUPAC, please contact, the Secretariat.
Questions regarding the website, please contact web
manager.