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Thioureas as Highly Active Catalysts for Biomimetic Bromocyclization of Geranyl Derivatives
Miyuki Terazaki1, Kei-Ichi Shiomoto1, Haruki Mizoguchi1
1Graduate School of Natural Science and Technology , Okayama University , 3-1-1, Tsushima-naka, Kita-ku, Okayama , Japan.
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 CH2Cl2 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.
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