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Copper-Catalysed, Enantioselective Desymmetrisation of meso Cyclic Allylic Bis(diethyl phosphates) with Organozinc Reagents

Piarulli, Umberto ; Daubos, Philippe ; Claverie, Christelle ; Monti, Chiara ; Gennari, Cesare

European Journal of Organic Chemistry, 2005-03, Vol.2005 (5), p.895-906 [Periódico revisado por pares]

Weinheim: WILEY-VCH Verlag

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  • Título:
    Copper-Catalysed, Enantioselective Desymmetrisation of meso Cyclic Allylic Bis(diethyl phosphates) with Organozinc Reagents
  • Autor: Piarulli, Umberto ; Daubos, Philippe ; Claverie, Christelle ; Monti, Chiara ; Gennari, Cesare
  • Assuntos: Allylic substitution ; Asymmetric synthesis ; Chiral ligands ; Copper ; meso Desymmetrisation ; Zinc
  • É parte de: European Journal of Organic Chemistry, 2005-03, Vol.2005 (5), p.895-906
  • Notas: istex:956A2D0588B7132E379F4540B9AFAE5A8C3B7D87
    ArticleID:EJOC200400757
    ark:/67375/WNG-F8MX6ZK3-H
  • Descrição: A highly regio‐, diastereo‐ and enantioselective desymmetrization of five‐, six‐, and seven‐membered meso, cyclic allylic bis(diethyl phosphates) (3–5) with organozinc reagents was developed, using catalytic amounts (10 mol%) of [Cu(OTf)]2·C6H6 and two different classes of chiral ligands: Schiff bases 1 and phosphoramidites 2. Good to excellent enantioselectivities were obtained for every substrate by a subtle balance of ligand structure and experimental conditions. In particular, ee’s of up to 88 % were obtained for the five‐membered ring substrate 3 with ligands 1cjo and 1cjm using Et2Zn (94 % ee with Me2Zn, 88 % ee with nBu2Zn). Schiff‐base ligands 1 were not effective with the six‐ and seven‐membered substrates 4 and 5. The use of phosphoramidite ligands 2 afforded ee’s of up to 94 % (Et2Zn) for the six‐membered ring product 7, and virtually only one enantiomer (ee ≥ 98 %, with Et2Zn) for the seven‐membered ring product 8. In addition, the desymmetrisation of the conduritol derivative 10 was obtained, with ee’s of up to 86 %. In this case, a fully functionalised cyclohexane derivative, containing four contiguous stereocentres and a double bond, was obtained as a single diastereomer and in high enantiomeric excess from an achiral starting material. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
  • Editor: Weinheim: WILEY-VCH Verlag
  • Idioma: Inglês
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