Abstract
Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98:2 d.r. using a readily available α‐amino acid‐derived azide. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.
Highlights
Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry
Mechanically interlocked molecules (MIMs)[3] have long been known[4,5] to display stereogenic units[6] as a result of the fixed relative orientation of achiral interlocked components,[7,8] or the topology of the mechanical bond itself,[9,10] the stereoselective synthesis of rotaxanes and catenanes exhibiting such stereochemistry remains largely unexplored,[11] with the vast majority reported as racemic mixtures, or separated using preparative chiral stationary phase HPLC (PCSP-HPLC).[12]
Okamoto and co-workers reported an enantioselective synthesis of an mechanically planar chiral (MPC) rotaxane by dynamic kinetic resolution in % 4 % e.e.[7e]. Lacour and co-workers reported the diastereoselective formation of a pseudorotaxane possessing a covalent and an MPC stereogenic element in % 8 % d.e.[13]
Summary
Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry. The development of stereoselective syntheses of mechanically planar chiral (MPC) rotaxanes, the stereogenic unit of which arises when a rotationally oriented macrocycle encircles a non-centrosymmetric axle, has proved challenging.
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