Issue 15, 2021

Site-selective binding of terpenoids within a confined space of metal–macrocycle framework: substrate-specific promotion or inhibition of cyclization reactions

Abstract

Site-selective adsorption of four terpenoids, (S)-citronellal, nerol, geraniol and farnesol, in a porous metal–macrocycle framework (MMF) was revealed by single-crystal X-ray diffraction analyses. When the cyclic reactions of these terpenoids were investigated, the cyclization reaction of (S)-citronellal was significantly promoted by MMF, but other cyclization reactions were completely suppressed even under the condition that an acid catalyst was fixed on the channel surface of MMF. Furthermore, in the reaction of the terpenoid mixture, (S)-citronellal was substrate-specifically cyclized. The promotion or inhibition of the terpenoid cyclization could be explained based on the difference in their binding structures to these MMF channels.

Graphical abstract: Site-selective binding of terpenoids within a confined space of metal–macrocycle framework: substrate-specific promotion or inhibition of cyclization reactions

Supplementary files

Article information

Article type
Research Article
Submitted
13 5月 2021
Accepted
07 6月 2021
First published
08 6月 2021

Org. Chem. Front., 2021,8, 4071-4077

Site-selective binding of terpenoids within a confined space of metal–macrocycle framework: substrate-specific promotion or inhibition of cyclization reactions

S. Tashiro, W. He, R. Hayashi, Y. Lin and M. Shionoya, Org. Chem. Front., 2021, 8, 4071 DOI: 10.1039/D1QO00750E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements