Highly selective and high-yielding rotaxane synthesis via aminolysis of prerotaxanes consisting of a ring component and a stopper unit

Keiji Hirose*, Keiji Nishihara, Naoki Harada, Yamato Nakamura, Daisuke Masuda, Masami Araki, Yoshito Tobe

*Corresponding author for this work

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

A highly rotaxane-selective synthesis via aminolysis of prerotaxanes, which were composed of a phenolic pseudo-crown ether as a ring component and a bulky stopper unit, was developed. The best result was obtained in the case of aminolysis of 3b with 3,5-dimethylbenzylamine which proceeded quantitatively with ca. 100% rotaxane selectivity forming the corresponding rotaxane 5b. The rotaxanes were formed by kinetically controlled attack of the amine from the backside of the ring component of the prerotaxanes.

Original languageEnglish
Pages (from-to)2969-2972
Number of pages4
JournalOrganic Letters
Volume9
Issue number16
DOIs
StatePublished - 2 Aug 2007

Fingerprint Dive into the research topics of 'Highly selective and high-yielding rotaxane synthesis via aminolysis of prerotaxanes consisting of a ring component and a stopper unit'. Together they form a unique fingerprint.

  • Cite this