Thioureas as Highly Active Catalysts for Biomimetic Bromocyclization of Geranyl Derivatives

Miyuki Terazaki, Kei Ichi Shiomoto, Haruki Mizoguchi, Akira Sakakura

Research output: Contribution to journalArticle

Abstract

Thioureas bearing electron-deficient aryl groups show high catalytic activity in the biomimetic bromocyclization of geranyl derivatives. The reaction of geranyl derivatives with N-bromosuccinimide (NBS) proceeds rapidly in CH 2 Cl 2 to give the corresponding bromocyclization products in high yields as a ca. 1:1 mixture of endo- and exo-isomers. The reactivity of geranyl derivatives highly depends on the terminal substituent: electron-donating substituents increase the reactivity, while electron-withdrawing substituents decrease the reactivity.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusPublished - Jan 1 2019

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Thiourea
Biomimetics
thioureas
biomimetics
reactivity
Electrons
Derivatives
catalysts
Isomers
Catalysts
Bearings (structural)
isomers
Bromosuccinimide
electrons
catalytic activity
Catalyst activity
methylidyne
products

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Thioureas as Highly Active Catalysts for Biomimetic Bromocyclization of Geranyl Derivatives. / Terazaki, Miyuki; Shiomoto, Kei Ichi; Mizoguchi, Haruki; Sakakura, Akira.

In: Organic Letters, 01.01.2019.

Research output: Contribution to journalArticle

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