UNIGE document Scientific Article
previous document  unige:5261  next document
add to browser collection
Title

Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: application of dynamic kinetic asymmetric transformation (DYKAT)

Authors
Published in Advanced Synthesis and Catalysis. 2010, vol. 352, no. 2-3, p. 447-457
Abstract The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd-catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper-catalyzed AAA. High enantioselectivities (up to 99% ee), scope of the reaction and mechanistic considerations are reported herein.
Keywords Allylic alkylationAllylic compoundsAsymmetric catalysisCopperNucleophilic substitution
Identifiers
Full text
Article (Published version) (254 Kb) - document accessible for UNIGE members only Limited access to UNIGE
Structures
Citation
(ISO format)
LANGLOIS, Jean-Baptiste, ALEXAKIS, Alexandre. Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: application of dynamic kinetic asymmetric transformation (DYKAT). In: Advanced Synthesis and Catalysis, 2010, vol. 352, n° 2-3, p. 447-457. https://archive-ouverte.unige.ch/unige:5261

217 hits

0 download

Update

Deposited on : 2010-02-23

Export document
Format :
Citation style :