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

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) [( R , R )-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)...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-02, Vol.70 (3), p.1011-1018
Main Authors: Ricci, Giacomo, Ruzziconi, Renzo, Giorgio, Egidio
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Summary: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) [( R , R )-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 1H 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 ( R , R )-1, while in the case of ( R , R )-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048147m