Enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution strategy

Ayumi Imayoshi, Bhatraju Vasantha Lakshmi, Yoshihiro Ueda, Tomoyuki Yoshimura, Aki Matayoshi, Takumi Furuta and Takeo Kawabata ()
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Ayumi Imayoshi: Kyoto University, Uji
Bhatraju Vasantha Lakshmi: Kyoto University, Uji
Yoshihiro Ueda: Kyoto University, Uji
Tomoyuki Yoshimura: Kanazawa University, Kakuma-machi
Aki Matayoshi: Kyoto University, Uji
Takumi Furuta: Kyoto University, Uji
Takeo Kawabata: Kyoto University, Uji

Nature Communications, 2021, vol. 12, issue 1, 1-7

Abstract: Abstract Asymmetric synthesis of mechanically planar chiral rotaxanes and topologically chiral catenanes has been a long-standing challenge in organic synthesis. Recently, an excellent strategy was developed based on diastereomeric synthesis of rotaxanes and catenanes with mechanical chirality followed by removal of the chiral auxiliary. On the other hand, its enantioselective approach has been quite limited. Here, we report enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution of the racemates via remote asymmetric acylation of a hydroxy group in the axis component, which provides an unreacted enantiomer in up to >99.9% ee in 29% yield (the theoretical maximum yield of kinetic resolution of racemate is 50%). While the rotaxane molecules are expected to have conformational complexity, our original catalysts enabled to discriminate the mechanical chirality of the rotaxanes efficiently with the selectivity factors in up to 16.

Date: 2021
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DOI: 10.1038/s41467-020-20372-0

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