Thioureas as highly active catalysts for biomimetic bromocyclization of geranyl derivatives

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

doi:10.1021/acs.orglett.9b00352

Thioureas as highly active catalysts for biomimetic bromocyclization of geranyl derivatives

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

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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- A nd 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 language	English
Pages (from-to)	2073-2076
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.9b00352
Publication status	Published - Apr 5 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Thioureas as highly active catalysts for biomimetic bromocyclization of geranyl derivatives",

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- A nd 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. ",

author = "Miyuki Terazaki and Shiomoto, {Kei Ichi} and Haruki Mizoguchi and Akira Sakakura",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Terazaki, Miyuki

AU - Shiomoto, Kei Ichi

AU - Mizoguchi, Haruki

AU - Sakakura, Akira

PY - 2019/4/5

Y1 - 2019/4/5

N2 - 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- A nd 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.

AB - 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- A nd 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.

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Thioureas as highly active catalysts for biomimetic bromocyclization of geranyl derivatives

Abstract

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