Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes | Zendy

Jinks Michael A. | Zendy; de Juan Alberto | Zendy; Denis Mathieu | Zendy; Fletcher Catherine J. | Zendy; Galli Marzia | Zendy; Jamieson Ellen M. G. | Zendy; Modicom Florian | Zendy; Zhang Zhihui | Zendy; Goldup Stephen M. | Zendy

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Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes

Author(s) -

Jinks Michael A.,

de Juan Alberto,

Denis Mathieu,

Fletcher Catherine J.,

Galli Marzia,

Jamieson Ellen M. G.,

Modicom Florian,

Zhang Zhihui,

Goldup Stephen M.

Publication year - 2018

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201808990

Subject(s) - stereocenter , rotaxane , stereoselectivity , chemistry , covalent bond , stereochemistry , azide , molecule , enantioselective synthesis , organic chemistry , supramolecular chemistry , catalysis

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.

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