Enantioselective Tail‐to‐Head Terpene Cyclizations by Optically Active Hexameric Resorcin[4]arene Capsule Derivatives. Issue 25 (22nd April 2022)

• Record Type: Journal Article
• Authors: Sokolova, Daria; Piccini, GiovanniMaria; Tiefenbacher, Konrad
• Is Part Of: Angewandte Chemie international edition. Volume 61:Issue 25(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-22
• Subjects: Chiral Self-Assemblies -- Enantioselective Catalysis -- Resorcinarene Capsules -- Supramolecular Catalysis -- Terpene Cyclization; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202203384
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Molecular capsules enable the conversion of substrates inside a closed cavity, mimicking to some extent enzymatic catalysis. Chirality transfer from the molecular capsule onto the encapsulated substrate has been only studied in a few cases. Here we demonstrate that chirality transfer is possible inside a rather large molecular container of approximately 1400 Å 3 . Specifically, we present 1) the first examples of optically active hexameric resorcin[4]arene capsules, 2) their ability to enantioselectively catalyze tail‐to‐head terpene cyclizations, and 3) the surprisingly high sensitivity of enantioselectivity on the structural modifications. Abstract : The first examples of enantioenriched hexameric resorcin[4]arene capsules have been synthesized. These large molecular containers, with an inner volume of approximately 1400 Å 3, enable the enantioselective tail‐to‐head cyclization of terpenes within their interior.