An Efficient Approach to Mechanically Planar Chiral Rotaxanes

2014/02/22 by R. J. Bordoli, Stephen M. Goldup · 1 voice · 2 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Chemical Synthesis and Analysis #Mass Spectrometry Techniques and Applications #Supramolecular Chemistry and Complexes

paper · doi:10.1021/ja412715m

openalex publication_date 2014/02/22 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/31

Abstract

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.

Cited by

• The End of the Beginning of Mechanical Stereochemistry
• A chiral macrocycle for the stereoselective synthesis of mechanically planar chiral rotaxanes and catenanes

Discussions

• I say 10 years because Rob Bordoli’s synthesis of chiral rotaxanes appeared in 2014 (dx.doi.org/10.1021/ja41...), although seeds were planted in 2011 by Hicham Lahlali when he saw an unexpectedly comp [bsky, 1 points, 1 comments]

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