Organic Letters
Organic Letters
5 years ago

Synthesis of Mechanically Planar Chiral rac-[2]Rotaxanes by Partitioning of an Achiral [2]Rotaxane: Stereoinversion Induced by Shuttling

Synthesis of Mechanically Planar Chiral rac-[2]Rotaxanes by Partitioning of an Achiral [2]Rotaxane: Stereoinversion Induced by Shuttling
Shinichi Saito, Katsuhiko Ikeyatsu, Shoichi Hosoya, Yuta Mochizuki, Yuichiro Mutoh
Mechanically planar chiral [2]rotaxanes were synthesized by the introduction of bulky pyrrole moieties into the axle component of an achiral [2]rotaxane. The enantiomers were separated by chiral HPLC. The shuttling of the ring component between the two compartments at high temperature induced the stereoinversion of the mechanically planar chiral [2]rotaxane. The rate of the stereoinversion was studied quantitatively, and the kinetic parameters were determined.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02043

DOI: 10.1021/acs.orglett.7b02043

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