Development of novel carbon-carbon bond forming reaction using the control of the reactivity of esters

2015 Fiscal Year Final Research Report

• Project/Area Number: 24350047
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Osaka University
• Principal Investigator: BABA Akio 大阪大学, 工学(系)研究科(研究院), 産学連携本部・特任教授(常勤) (20144438)
• Co-Investigator(Kenkyū-buntansha): NISHIMOTO Yoshihiro 大阪大学, 大学院工学研究科, 助教 (30550115)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: エステル / 新規有機合成反応

Outline of Final Research Achievements

We have developed Mukaiyama aldol reaction directly using esters. The three components, an ester, a silyl enolate, and a hydrosilane treated with indium triiodide to give the corresponding Mukaiyama aldol product. Indium triiodide accelerates the hydrosilation of esters and the addition of silyl enolates to resulted aldehydes. Various types of esters and silyl enolates were applicable to this reaction system. The use of amides instead of esters effectively provided aminocarbonyl compounds. In addition, we have revealed that a sequential addition of silyl cyanide and ketene silyl acetals to esters was achieved by a gallium trihalide catalyst to produce β-cyano-β-siloxy esters.

Free Research Field

有機化学