Highly enantioselective synthesis of 2-furanyl-hydroxyacetates from furans via the Friedel-Crafts reaction

Org Lett. 2008 Jul 17;10(14):2955-8. doi: 10.1021/ol800927w. Epub 2008 Jun 24.

Abstract

The Friedel-Crafts reaction of alkyl glyoxylates with variously substituted furans was found to be efficiently catalyzed under simple, undemanding conditions by a 6,6'-dibromo-BINOL/Ti(IV) complex with high enantioselectivity. The reaction afforded chiral substituted 2-furanyl-hydroxyacetic acid esters, compounds of high synthetic interest, in good yield and enantiomeric excess, in most examples in the range of 90-97%.