Tris(2,6-diphenylbenzyl)amine (TDA) and tris(2,6-diphenylbenzyl)phosphine (TDP) with unique bowl-shaped structures: synthetic application of functionalized TDA to chemoselective silylation of benzylic alcohols

摘要

A new strategy for obtaining the formal steric hindrance of tertiary amines by remote steric factors is described by designing the bowl-shaped,structurally unique tris(2,6-diphenylbenzyl)amine (TDA).In addition ot its structural uniqueness,TDA possesses the rich electronic atmosphere derived from three 2,6-diphenylbenzyl moieties,thereby allowing the chemoselective silylation of benzylic alcohols preferentially over other alcohosl based on the effective aromatic #pi#,#pi# interaction.This approach of preparing TDA is also applicable to the new synthesis of tris(2,6-diphenylbenzyl)phosphine (TDP).