136409-95-5Relevant articles and documents
Highly selective primary alkoxycarboxylation and esterification of unprotected pyranose derivatives mediated by scandium(III) triflate catalysis
McClure, Michael S.,Berry, Malcolm B.,Caine, Darren,Crawford, Claire,Crump, Brian C.,Glover, Bobby N.,Kedia, Sandeep B.,Millar, Alan,Mitchell, Mark B.,Nichols, Christopher J.,Patterson, Daniel E.,Powers, Jeremiah
supporting information; experimental part, p. 3561 - 3565 (2012/07/27)
A highly selective method for the alkoxycarboxylation and acylation of primary alcohols of pyranose derivatives is described. The reaction is high yielding and proceeds under mild conditions with 0.15-1 mol-% Sc(OTf) 3 used in combination with anhydrides or pyrocarbonates at 40-50 °C. Selectivities observed for alkoxycarboxylation of unprotected pyranose derivatives are > 95 and this constitutes a significant advantage over existing methods. Mechanistic implications, including the role of steric demand and metal-heteroatom coordination are also discussed.
