以手征性联萘为模板合成一种新的螺旋环芳分子

基于2,2'-二取代的联萘衍生物在手性构型上高度稳定的特点, 分别从光学活性的(R)-和(S)-2,2'-二乙炔基-1,1'-联萘结构模板出发, 通过Sonogashira 偶连反应导入苄基砜, 然后用二异丙基氨基锂(LDA)处理制得的联萘二砜成功地合成了一种新的螺旋环芳分子——对映异构体(R,P)-3和(S,M)-3. MS, IR, ¹H和¹³C NMR以及元素分析表征了这些化合物．镜象特征的圆二色(CD)谱和比旋光度α]_D的测定结果清楚地反映了它们的对映异构关系．

Synthesis of a Novel Helical Cyclophane Using Chiral Binaphthyl as Structural Templates

The chiral binaphthyls is one of the most important precursors for constructing optical molecules. In this paper, (R)- and (S)-2,2'-diethynyl-1,1'-binaphthyl with highly stable chiral configurations were employed as structural templates, and a new type of helical cyclophane compounds (R,P)-3 and (S,M)-3 were synthesized in enantiopure form by the introduction of benzyl sulfone through Sonogashira coupling reaction, followed by the treatment of disulfone with lithium diisopropylamide (LDA). MS, IR, ¹H and ¹³C NMR as well as elemental analysis characterized compound 3. The enantiomeric relation of two isomers was reflected unambiguously by their circular dichroism spectra with exact mirror images and specific rotations α]_D data.