Tocopherol side chain synthesis via asymmetric organocatalytic transfer hydrogenation and convenient measurement of stereoselectivity

Abstract

An asymmetric synthetic route for 1-iodofarnesane, a key intermediate for tocopherol side chain synthesis, starting from (+)-(R)-citronellal was developed. 1-Iodofamesane was prepared through eight steps in about 50% overall yield, and asymmetric transfer hydrogenation of the enal with a chiral organocatalyst was conducted as a stereoinduction step. To measure the stereoinduction level and optical purity of the product, a convenient analytical method was developed in which a phenylcarbamate derivative of the C-15 alcohol was found to be suitable to give proper polarity and UV-activity for chiral UV-HPLC analysis. (C) 2014 Elsevier Ltd. All rights reserved.