Organic Chemistry

A Co-conformationally “Topologically” Chiral Catenane



As recognized in the early 1960s, catenanes composed of two achiral rings that are oriented (Cnh symmetry) as a result of the sequence of atoms they contain are topologically chiral. Here we present the first synthesis of a highly enantioenriched catenane containing a related but overlooked “co-conformationally ‘topologically’ chiral” stereogenic unit, which arises when a bilaterally symmetric Cnv ring is desymmetrised by the position of an oriented macrocycle.


Thumbnail image of MS CCTC catenane Rubio ChemRxiv.pdf

Supplementary material

Thumbnail image of ESI Rubio CCTC ChemRxiv.pdf
Electronic supporting information
Supporting information including characterisation data for all novel compounds and extended discussion
Thumbnail image of rac-(S,Smt)-3b.cif
cif for rac-(S,Smt)-3b
crystallographic data for rac-(S,Smt)-3b
Thumbnail image of rac-6.cif
cif for rac-6
crystallographic data for rac-6
Thumbnail image of rac-9 .cif
cif for rac-9
crystallographic data for rac-9

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