Asymmetric Synthesis of Highly Functionalized Chiral Silicon Molecules and Application Thereof

2015 Fiscal Year Final Research Report

• Project/Area Number: 24350048
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Kyushu University
• Principal Investigator: Igawa Kazunobu 九州大学, 先導物質化学研究所, 助教 (80401529)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: 不斉合成 / 有機ケイ素分子 / ケイ素キラリティー / 生理活性

Outline of Final Research Achievements

A variety of novel chiral silicon molecules were synthesized in optically active form by highly enantioselective asymmetric desymmetrization of achiral silicon molecules and further stereoselective transformations. 1) Enantioselective hydrosilylation of dihydrosilanes with a chiral platinum catalyst afforded chiral alkenylhydrosilanes in optically active form up to 86% ee, which were converted into chiral silanols in highly stereoselective manner. 2) Enantioselective beta-elimination of silacyclopentene oxides with a novel chiral lithium amide afforded chiral silacyclopentenols in optically active form up to >98% ee, which were converted in to a variety of chiral silacyclopentane derivatives. One of the synthesized silacyclopentane derivatives showed substantial binding activity to a serotonin receptor protein, in which the silicon chirality is the key structural factor for the binding activity.

Free Research Field

有機合成化学