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Igawa K, Yoshihiro D, Abe Y, et al. Enantioselective Synthesis of Silacyclopentanes. Angew Chem Int Ed Engl. 2016;55(19):5814-8doi: 10.1002/anie.201511728.
Igawa, K., Yoshihiro, D., Abe, Y., & Tomooka, K. (2016). Enantioselective Synthesis of Silacyclopentanes. Angewandte Chemie (International ed. in English), 55(19), 5814-8. https://doi.org/10.1002/anie.201511728
Igawa, Kazunobu, et al. "Enantioselective Synthesis of Silacyclopentanes." Angewandte Chemie (International ed. in English) vol. 55,19 (2016): 5814-8. doi: https://doi.org/10.1002/anie.201511728
Igawa K, Yoshihiro D, Abe Y, Tomooka K. Enantioselective Synthesis of Silacyclopentanes. Angew Chem Int Ed Engl. 2016 May 04;55(19):5814-8. doi: 10.1002/anie.201511728. Epub 2016 Apr 01. PMID: 27037672.
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Angew Chem Int Ed Engl. 2016 May 04;55(19):5814-8. doi: 10.1002/anie.201511728. Epub 2016 Apr 01.

Enantioselective Synthesis of Silacyclopentanes.

Angewandte Chemie (International ed. in English)

Kazunobu Igawa, Daisuke Yoshihiro, Yusuke Abe, Katsuhiko Tomooka

Affiliations

  1. Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka, 816-8580, Japan. [email protected].
  2. Department of Molecular and Material Sciences, Kyushu University, Japan.
  3. Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka, 816-8580, Japan. [email protected].

PMID: 27037672 DOI: 10.1002/anie.201511728

Abstract

A variety of functionalized silacyclopentanes were synthesized by highly enantioselective β-eliminations of silacyclopentene oxides followed by stereospecific transformations. The reaction mechanism of the β-elimination was elucidated by DFT calculations. An in vitro biological assay with an oxy-functionalized silacyclopentane showed substantial binding to a serotonin receptor protein.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: asymmetric synthesis; biological activity; chirality; elimination; silicon

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