Organic Chemistry Portal

Abstracts

Search:

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)


see article for more reactions

Abstract

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%.

see article for more examples



Key Words

Corey-Chaykovsky Reaction, Epoxides


ID: J54-Y2010-0350