A highly chemoselective Mukaiyama aldol reaction of saturated aldehyde over unsaturated aldehyde with enol tris (2,6-diphenylbenzyl) silyl ether

摘要

An exceedingly high chemoselective Mukaiyama aldol reaction of saturated aldehydes in the presence of unsaturated aldehydes (benzaldehyde and #alpha#,#beta#-enals) has been realized for the first time by using the structurally unique enol tris (2,6-diphenylbenzyl) silyl ether under the influence of BF_3OEt_2 as a Lewis acid. Among unsaturated aldehydes, benzaldehyde is found to be more reactive than #alpha#,#beta#-enals. The structural uniqueness of the enol tris (2,6-diphenylbenzyl) silyl ether can be visualized by X-ray crystallography as well as ~1H and ~(13)C NMR spectroscopy.