Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 32, Pages 5622-5634Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900774
Keywords
Asymmetric catalysis; Cycloaddition; Azomethine ylides; Silver; Phosphorus
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Funding
- Spanish Ministerio de Educacion y Ciencia (MEC) [Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU, CTQ2004-00808/BQU]
- University of Alicante
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The endo-diastereo- and enantioselective 1,3-dipolar cyclo-addition of azomethine ylides and electrophilic alkenes is efficiently catalysed by chiral phosphoramidite-silver(I) perchlorate complexes. The reaction allows the presence of different types of substituents in the 1,3-dipole and can be applied to the synthesis of enantiomerically enriched, highly substituted prolines. This methodology was applied to the total synthesis of the inhibitors of the hepatitis C virus (HCV). Computational studies support a two-step mechanism predicting exactly the experimental results and the origin of both the diastereo- and enantioselections, as well as a reasonable explanation concerning the different reaction rates observed for some substrates. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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