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  1. P. Müller, D. Riegert,
    “Desymmetrization of spiroactivated meso-cyclopropanes via nucleophilic substitution”
    Tetrahedron 2005, 61, 4373-4379.

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.

DOI : 10.1016/j.tet.2005.03.005 

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