Enantioselective Synthesis of Silacyclopentanes

Kazunobu Igawa; Daisuke Yoshihiro; Yusuke Abe; Katsuhiko Tomooka

doi:10.1002/anie.201511728

Enantioselective Synthesis of Silacyclopentanes

Kazunobu Igawa, Daisuke Yoshihiro, Yusuke Abe, Katsuhiko Tomooka

Department of Applied Molecular Chemistry

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

33 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5814-5818
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	19
DOIs	https://doi.org/10.1002/anie.201511728
Publication status	Published - May 4 2016

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/anie.201511728

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title = "Enantioselective Synthesis of Silacyclopentanes",

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.",

author = "Kazunobu Igawa and Daisuke Yoshihiro and Yusuke Abe and Katsuhiko Tomooka",

note = "Funding Information: This research was supported by JSPS KAKENHI Grants (24350048, 15K13697, 15J07532), and the MEXT Project of Integrated Research on Chemical Synthesis. We thank T. Nishi (IMCE, Kyushu University) for the HRMS measurements. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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T1 - Enantioselective Synthesis of Silacyclopentanes

AU - Igawa, Kazunobu

AU - Yoshihiro, Daisuke

AU - Abe, Yusuke

AU - Tomooka, Katsuhiko

N1 - Funding Information: This research was supported by JSPS KAKENHI Grants (24350048, 15K13697, 15J07532), and the MEXT Project of Integrated Research on Chemical Synthesis. We thank T. Nishi (IMCE, Kyushu University) for the HRMS measurements. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Y1 - 2016/5/4

N2 - 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.

AB - 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.

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ER -

Enantioselective Synthesis of Silacyclopentanes

Abstract

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