Highly Selective Preparation of (E)- and (Z)- Silyl Enol Ethers from Wittig Reaction of Salt-Free Phosphonium Ylide Generated by 1,2-Brook Rearrangement

2015 Fiscal Year Final Research Report

• Project/Area Number: 26860011
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: University of Toyama
• Principal Investigator: Minato Daishiro 富山大学, 大学院医学薬学研究部(薬学), 助教 (80610914)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: Brook転位 / Wittig反応 / ホスフィン / イリド / 炭素間結合反応 / シリルエノールエーテル

Outline of Final Research Achievements

The target of this study is to develop new methodologies for the molecular transformation based on the intramolecular silyl group rearrangement reaction, so-called Brook rearrangement. In searching for various conditions, the reaction of acylsilanes with phosphine nucleophiles which afforded phosphonium ylides through 1,2-Brook rearrangement was found. A Wittig reaction of the resulting phosphonium ylides and aldehydes or imines proceeded successively and afforded silyl enol ethers with high stereoselectivity.

Free Research Field

有機化学