Enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution strategy

• DOI: 10.1038/s41467-020-20372-0
• Publication Date: 2021-01-15T11:03:35Z
• Authors: Ayumi Imayoshi; Bhatraju Vasantha...; Yoshihiro Ueda; Tomoyuki Yoshimura; Aki Matayoshi; Takumi Furuta; Takeo Kawabata
• Keywords: Kinetic resolution

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