Atropisomeric (R,R)-2,2 '-Bi([2]paracyclo[2](5,8)quinolinophane) and (R,R)-1,1 '-Bi([2]paracyclo[2](5,8)isoquinolinophane): Synthesis, structural analysis, and chiroptical properties

作者：Ricci G; Ruzziconi R^*; Giorgio E

来源：Journal of Organic Chemistry, 2005, 70(3): 1011-1018.

DOI：10.1021/jo048147m

Atropisomeric (R,R)-2,2'-bi([2]paracyclo[2](5,8)quinolinophane) [(R,R)-1] and (R,R)-1,1'-bi([2]-paracyclo[2](5,8)isoquinolinophane) [(RR)-2] have been prepared in moderate overall yield (17 and 9%, respectively) by a four-step sequence starting from (R)-(-)-4-amino[2.2]paracyclophane and (R)-(-)-4-carboxy[2.2]paracyclophane, respectively. The structures have been determined on the basis of NOE H-1 NMR analysis and molecular mechanics (MM) calculations performed with a Spartan02 program, using the MMF94s force field. A preliminary, qualitative analysis of the chiroptical properties of these two compounds has also been attempted. The main spectral data can be interpreted in terms of an almost planar 2,2'-bisquinoline chromophore inserted in a paracyclophane structure in the case of (RR)-1, while in the case of (RR)-2, the main role is played by a distorted 1,1'-bisisoquinoline chromophore. On the basis of the above structural results, a hypothesis about the enantioselection capability of these two molecules has also been formulated.

• 出版日期2005-2-4