Controlling mechanical geometrical isomerism in rotaxanes Andrea Savoini, Peter Gallagher, John R. J. Maynard, Patrick Butler, Graham Tizzard and Stephen M. Goldup University of Southampton, UK The orientation of a macrocycle with distinct faces on the axle of a rotaxane can give rise to mechanical geometrical and mechanically axial chiral stereoisomers. 1 The isomerism arises from the threading of a facially dissymmetric macrocycle (C nv symmetry) with an oriented axle (C nv symmetry) and a bilaterally symmetric axle (C s ) respectively. Neither form has been studied significantly. 2 Recently, our group reported the first stereoselective synthesis of a mechanically axially chiral catenane and the rotaxane analogue. 3 Here we reported a study of the factors that controls the selectivity of the synthesis of both form of isomerism, leading to the first enantioselective synthesis of a mechanically axially chiral rotaxane. 4
References 1. H. L. Frisch and E. Wasserman, J. Am. Chem. Soc. , 1961, 83 , 3789–3795. 2. E. M. G. Jamieson, F. Modicom and S. M. Goldup, Chem. Soc. Rev , 2018, 47 , 5266–5311. 3. J. R. J. Maynard, P. Gallagher, D. Lozano, P. Butler and S. M. Goldup, Nat.Chem , 2022, 14 , 1038-1044 4. A. Savoini, P. Gallagher, J. R. J. Maynard, P. Butler, G. Tizzard and S. M. Goldup, Manuscript in preparation.
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