Catalytic (Asymmetric) Methylene Transfer to Aldehydes
Alessandro Piccinini, Sarah A. Kavanagh, Paul B. Connon and Stephen J. Connon*
*Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland, Email: connonstcd.ie
A. Piccinini, S. A. Kavanagh, P. B. Connon, S. J. Connon, Org. Lett., 2010, 12, 608-611.
DOI: 10.1021/ol902816w (free Supporting Information)
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Methyl triflate rapidly alkylates cyclic thiolanes under mild conditions, allowing their use in catalytic amounts in efficient aldehyde epoxidation reactions (in conjunction with phosphazene bases) at loadings as low as 10 mol%.
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