An Efficient Approach to Mechanically Planar Chiral Rotaxanes

We
describe the first method for production of mechanically planar
chiral rotaxanes in excellent enantiopurity without the use of chiral
separation techniques and, for the first time, unambiguously assign
the absolute stereochemistry of the products. This proof-of-concept
study, which employs a chiral pool sugar as the source of asymmetry
and a high-yielding active template reaction for mechanical bond formation,
finally opens the door to detailed investigation of these challenging
targets.