Development of a Method for Efficient Preparation of Chiral Silver Enolates

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410107
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Chiba University
• Principal Investigator: YANAGISAWA Akira 千葉大学, 理学(系)研究科(研究院), 教授 (60183117)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 有機化学 / 触媒・化学プロセス / 不斉反応 / エノラート / キラル触媒

Outline of Final Research Achievements

We have examined methods for efficiently generating silver(I) methoxide as well as methods for preparing silver(I) enolates from the methoxide. As a result, we have found that the Hunig base is effective as an additive for the purpose and desired silver(I) methoxide and the corresponding silver(I) enolates can be prepared with high purities. When an optically active phosphine compound has been used as an asymmetric ligand for silver(I) methoxide and a Mannich-type reaction via a chiral silver(I) enolate catalyzed by the chiral silver(I) methoxide has been performed, a high level of asymmetric induction has been observed for the Mannich product. Asymmetric α-amination and asymmetric aldol reaction have been also attained by applying the present catalytic method of generating chiral silver(I) enolates to various electrophiles. Further studies of diverse asymmetric reactions utilizing this catalytic system are underway.

Free Research Field

有機合成化学