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Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes.

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.

SUBMITTER: Jinks MA

PROVIDER: S-EPMC6220991 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes.

Jinks Michael A MA de Juan Alberto A Denis Mathieu M Fletcher Catherine J CJ Galli Marzia M Jamieson Ellen M G EMG Modicom Florian F Zhang Zhihui Z Goldup Stephen M SM

Angewandte Chemie (International ed. in English) 20181017 45

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. ...[more]

PMID: 30253008

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A chiral interlocking auxiliary strategy for the synthesis of mechanically planar chiral rotaxanes.

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Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy.

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