Synthesis of Chiral β‐Hydroxy Selenides by Ruthenium‐catalysed Transfer Hydrogenation of α‐Aryl Selenomethyl Ketones

A highly efficient transfer hydrogenation of α-aryl selenomethyl ketones to chiral β-hydroxy selenides catalysed by chiral diamine-derived ruthenium complex with a mixture of formic acid and triethylamine as a hydrogen source is described.

Abstract

A highly efficient transfer hydrogenation of α-aryl selenomethyl ketones, using readily available chiral diamine-derived ruthenium complex as a catalyst and a mixture of formic acid and triethylamine as a hydrogen source in dichloromethane under ambient conditions, is described. A wide range of chiral β-hydroxy selenides was obtained in 90–99% ee values and moderate to good yields. The practicability is also demonstrated by a gram-scale synthesis and downstream derivatization.