Enantioselective Synthesis of Silacyclopentanes. Issue 19 (1st April 2016)

• Record Type: Journal Article
• Authors: Igawa, Kazunobu; Yoshihiro, Daisuke; Abe, Yusuke; Tomooka, Katsuhiko
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 19(2016)
• Page Start: 5814
• Page End: 5818
• Publication Date: 2016-04-01
• Subjects: asymmetric synthesis -- biological activity -- chirality -- elimination -- silicon; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201511728
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Silacyclopentene oxides were converted into functionalized silacyclopentanes by highly enantioselective β‐elimination followed by various stereospecific transformations. The reaction mechanism of the β‐elimination was analyzed by DFT calculations. A hydroxy‐substituted silacyclopentane showed substantial binding to a serotonin receptor protein in an in vitro assay.