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.

We present a simple approach to bipyridine macrocycles in remarkable yields (typically >65%) and demonstrate their application in efficient rotaxane synthesis.

Correction for ‘High yielding synthesis of 2,2′-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes’ by J. E. M. Lewis et al., Chem. Sci., 2016, DOI: 10.1039/c6sc00011h.