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Enantioselective Tail-to-Head Terpene Cyclizations by Optically Active Hexameric Resorcin[4]arene Capsule Derivatives.

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 Å³ . 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.

SUBMITTER: Sokolova D

PROVIDER: S-EPMC9323437 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Enantioselective Tail-to-Head Terpene Cyclizations by Optically Active Hexameric Resorcin[4]arene Capsule Derivatives.

Sokolova Daria D Piccini GiovanniMaria G Tiefenbacher Konrad K

Angewandte Chemie (International ed. in English) 20220422 25

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<sup>3</sup> . Specifically, we present 1) the first examples of optically active hexameric resorcin[4]arene capsules, 2) their ability to ...[more]

PMID: 35324038

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