Hydroformylation of Olefinic Derivatives of Isosorbide and Isomannide

J Org Chem. 2016 Sep 2;81(17):7510-7. doi: 10.1021/acs.joc.6b01179. Epub 2016 Aug 10.

Abstract

The first time application of hydroformylation on olefinic derivatives of isosorbide and isomannide is shown by which a new carbon-carbon bond is formed. Depending on the ligand and reaction conditions used, the C6 regioisomer a can be obtained in 4:1 ratio and excellent yield, whereas C5 isomer b is achieved in almost complete regioselectivity (46:1) and good yield. In the majority of cases only the exo orientation is observed for the obtained aldehydes, and the method is easily applicable also on a 1 g scale.

Publication types

  • Research Support, Non-U.S. Gov't