Enantioselective Synthesis of Silacyclopentanes

Kazunobu Igawa; Daisuke Yoshihiro; Yusuke Abe; Katsuhiko Tomooka

doi:10.1002/anie.201511728

Enantioselective Synthesis of Silacyclopentanes

Angew Chem Int Ed Engl. 2016 May 4;55(19):5814-8. doi: 10.1002/anie.201511728. Epub 2016 Apr 1.

Authors

Kazunobu Igawa¹, Daisuke Yoshihiro², Yusuke Abe², Katsuhiko Tomooka³

Affiliations

¹ Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka, 816-8580, Japan. kigawa@cm.kyushu-u.ac.jp.
² Department of Molecular and Material Sciences, Kyushu University, Japan.
³ Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka, 816-8580, Japan. ktomooka@cm.kyushu-u.ac.jp.

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.

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

Publication types

Research Support, Non-U.S. Gov't