Synthesis of enantiopure planar chiral bis-(para)-pseudo-meta-type [2.2]paracyclophanes.

Chirality

Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, Japan.

Published: October 2018

A new type of planar chiral (R )- and (S )-4,7,12,15-tetrasubstituted [2.2]paracyclophanes was prepared from racemic 4,7,12,15-tetrabromo[2.2]paracyclophane as the starting substrate. Regioselective lithiation and transformations afforded racemic bis-(para)-pseudo-meta-type [2.2]paracyclophane (4,15-dibromo-7,12-dihydroxy[2.2]paracyclophane). Its optical resolution was performed by the diastereomer method using a chiral camphanoyl group as the chiral auxiliary. The diastereoisomers were readily isolated by simple silica gel column chromatography, and the successive hydrolysis afforded (R )- and (S )-bis-(para)-pseudo-meta-type [2.2]paracyclophanes ((R )- and (S )-4,15-dibromo-7,12-dihydroxy[2.2]paracyclophanes). They can be used as pseudo-meta-substituted chiral building blocks.

Download full-text PDF

Source
http://dx.doi.org/10.1002/chir.23010DOI Listing

Publication Analysis

Top Keywords

planar chiral
8
chiral
5
synthesis enantiopure
4
enantiopure planar
4
chiral bis-para-pseudo-meta-type
4
bis-para-pseudo-meta-type [22]paracyclophanes
4
[22]paracyclophanes type
4
type planar
4
chiral -471215-tetrasubstituted
4
-471215-tetrasubstituted [22]paracyclophanes
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!