OL21_7_2073.pdf 475 KB
Terazaki, Miyuki Graduate School of Natural Science and Technology, Okayama University
Shiomoto, Kei-ichi Graduate School of Natural Science and Technology, Okayama University
Mizoguchi, Haruki Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID
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.
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher.
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© American Chemical Society
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Org. Lett. 2019, 21, 7, 2073-2076 Publication Date:March 12, 2019 https://doi.org/10.1021/acs.orglett.9b00352