A chiral interlocking auxiliary strategy for the synthesis of mechanically planar chiral rotaxanes.

ABSTRACT: Rotaxanes can display molecular chirality solely due to the mechanical bond between the axle and encircling macrocycle without the presence of covalent stereogenic units. However, the synthesis of such molecules remains challenging. We have discovered a combination of reaction partners that function as a chiral interlocking auxiliary to both orientate a macrocycle and, effectively, load it onto a new axle. Here we use these substrates to demonstrate the potential of a chiral interlocking auxiliary strategy for the synthesis of mechanically planar chiral rotaxanes by producing a range of examples with high enantiopurity (93-99% e.e.), including so-called 'impossible' rotaxanes whose axles lack any functional groups that would allow their direct synthesis by other means. Intriguingly, by var

SUBMITTER: de Juan A 

PROVIDER: S-EPMC7612332 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature