The Development of an Environmentally Friendly and Mild Synthesis Method for Furans

2014 Fiscal Year Final Research Report

• Project/Area Number: 24550055
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Hiroshima University
• Principal Investigator: KOJIMA Satoshi 広島大学, 理学(系)研究科(研究院), 准教授 (70215242)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: フラン / 弱酸 / 第4級炭素 / ジカルボニル化合物 / 環境調和 / 8－フェニルメンチル基 / ジアステレオ選択性

Outline of Final Research Achievements

For reactions using 2-benzyloxycarbonylcyclopentanone as the donor and cis-4-oxo-2-pentenal as the acceptor, the Michael addition reaction had been found to occur in the presence of base. However, in the absence of base, furans bearing a quaternary carbon substituent in the 2-position were found to form under the mild temperature condition of room temperature. The furan forming reaction was found to be accelerated in the presence of weak acids such as hexafluoroisopropyl alcohol and benzoic acid. Asymmetric reactions using the 8-phenylmenthyl group as a chiral auxiliary was found to proceed with diastereoselectivity up to 96% de.

Free Research Field

有機化学