以(R)-叔丁基亚磺酰胺为手性助剂,与1,3-苯二甲醛经缩合反应制得关键中间体——(Rs,Rs)-双叔丁基亚磺酰亚胺(7);锂化的羧酸酯与7经不对称加成反应合成了两个新型的Rh2(esp)2配体类似物——(Rs,Rs',R,R')-β-胺基羧酸酯和(Rs,Rs',R,R',R,R')-α,β-氮杂环丙烷羧酸酯,产率分别为96%和65%,非对映选择性均大于20∶1。化合物的结构经1H NMR和13C NMR表征。
A synthetic approach toward the enantioenriched analogues of α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid which was the ligand of Rh2( esp)2catalyst was reported. In this process,the chiral( R)-tert-butanesulfinyl diimine derived from 1,3-benzenedialdehyde was used in the nucleophilic additions of lithium ester enolates to give two novel chiral analogues of the "esp"esters that are( Rs,Rs',R,R')-β-amino esters and( Rs,Rs',R,R',R,R')-α,β- aziridinyl esters in yields of 96%and 65% with excellent diastereoselectivity( dr 20 ∶ 1). The structures were characterized by1 H NMR and13 C NMR.