Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides.

Feilong He,Junxia Yang,Ping Deng,Yan Xiong,Hui Zhou,Guojuan Liang,Guanghui Chen

doi:10.1039/c8ra00552d

Abstract

A pre-prepared Ni–PyBisulidine complex has been developed for the catalytic asymmetric Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides. The corresponding β-nitro-α-hydroxy esters were obtained in good to excellent yields (up to 99%) with a high enantiomeric excess (ee) (up to 94%) with a catalyst loading of 1–2 mol%. The desired products of 2-acylpyridines and 2-acylpyridine N-oxides, which were simple methyl ketones, were obtained in medium to excellent yields (up to 94%) with medium to good ee (up to 86%) by using 2 mol% of catalyst.

Highlights

The Henry reaction is one of the important methods for C–C bond formation.[1]
Increasing efforts have been directed towards developing a catalytic asymmetric Henry reaction.[2]
Tosaki et al reported the kinetic resolution of racemic derivatives,[4] the catalytic asymmetric Henry reaction of simple ketones is rarely reported

Summary

Introduction

The Henry reaction is one of the important methods for C–C bond formation.[1]. The resulting products, b-nitroalcohols, are key intermediates and building blocks for the synthesis of bioactive natural products and pharmaceutical agents.[1].

Results

Conclusion