Boroxine template for macrocyclization and postfunctionalization.

Abstract

A novel synthetic strategy for large macrocyclic molecules using boroxine formation was developed. For this, the threefold intramolecular olefin metathesis of 3,5-bis(alkenyloxy)phenylboroxines with various lengths of alkenyl chains, formed by the dehydration of the corresponding boronic acid substrates, together with treatment with pinacol, was used to produce 39-, 45-, and 51-membered macrocyclic compounds with three boronate units. The boroxine moiety functions as a covalent template but can also be used to postmodify the macrocycle. Boroxine-templated macrocyclization implemented in this way does not require the addition of template molecules and simplifies the synthetic procedure.

• Authors: Kosuke Ono, Satoru Onodera, Hidetoshi Kawai
• Journal: Chemical communications (Cambridge, England) (Chem Commun (Camb)) Vol. 58 Issue 90 Pg. 12544-12547 (Nov 10 2022) ISSN: 1364-548X [Electronic] England
• PMID: 36214271 (Publication Type: Journal Article)

Chemical References

• Macrocyclic Compounds
• Alkenes
• Boronic Acids

Topics

• Macrocyclic Compounds (chemistry)
• Alkenes (chemistry)
• Boronic Acids (chemistry)