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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:

A. Piccinini, S. A. Kavanagh, P. B. Connon, S. J. Connon, Org. Lett., 2010, 12, 608-611.

DOI: 10.1021/ol902816w

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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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Key Words

Corey-Chaykovsky Reaction, Epoxides

ID: J54-Y2010-0350