2012 using (1R,2S,5R)-(–)-menthyl (S)-p-toluenesulfinate as a chiral auxiliary [31],
as shown in Fig. 3.3, and the obtained diastereomers could be used as the parent
compounds to produce a wide variety of [2.2]paracyclophane-based chiral molecules. Optical resolution of rac-pseudo-ortho-disubstituted [2.2]paracyclophanes by
chiral columns was reported [32]. The chromatographic optical resolution of racpseudo-meta-disubstituted [2.2]paracyclophanes was also reported by Lutzen, and
several enantiopure pseudo-meta-disubstituted [2.2]paracyclophanes were produced
[33]. Figure 3.4 shows the representative examples of the successful optical resolutions obtained using a chiral column.
In 2008, Hopf and coworkers reported the optical resolutions of bis-(ortho)pseudo-meta-4,5,15,16-tetrasubstituted
[2.2]paracyclophane
and
4,5,15Fig. 3.3 Optical resolution of pseudo-ortho-disubstituted [2.2]paracyclophane using (1R,2S,5R)(–)-menthyl (S)-p-toluenesulfinate as a chiral auxiliary
Fig. 3.4 Optical resolution of rac-pseudo-meta-disubstituted [2.2]paracyclophane
34
Y. Morisaki