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Desymmetrization of spiroactivated meso-cyclopropanes via nucleophilic substitution

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Published in Tetrahedron. 2005, vol. 61, no. 18, p. 4373-4379
Abstract The spiro-activated cyclopropane 1 undergoes desymmetrization either with Li-thiophenoxide in the presence of a chiral complexing ligand, or with ion pairs formed from thiophenols and aromatic chiral amines. The latter procedure is more efficient and provides the ring-opened thioether 6 in up to 79% yield and up to 60% ee.
Keywords Nucleophilic substitutionChiral ion pairsThiophenoxideChiral ligandChinchonine
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MULLER, Paul, RIEGERT, David. Desymmetrization of spiroactivated meso-cyclopropanes via nucleophilic substitution. In: Tetrahedron, 2005, vol. 61, n° 18, p. 4373-4379. https://archive-ouverte.unige.ch/unige:6972

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Deposited on : 2010-06-18

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