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Scientific article
English

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

Published inAdvanced synthesis & catalysis, vol. 352, no. 2-3, p. 447-457
Publication date2010
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 alkylation
  • Allylic compounds
  • Asymmetric catalysis
  • Copper
  • Nucleophilic substitution
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 & catalysis, 2010, vol. 352, n° 2-3, p. 447–457. doi: 10.1002/adsc.200900790
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Article (Published version)
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ISSN of the journal1615-4150
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