Cooperative Brnsted Acid-Type Organocatalysis: Alcoholysis of Styrene Oxides
详细信息 查看全文
- 作者：Torsten Weil ; Mike Kotke ; Christian M. Kleiner ; Peter R. Schreiner
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：April 17, 2008
- 年：2008
- 卷：10
- 期：8
- 页码：1513 - 1516
- 全文大小：117K
- 年卷期：v.10,no.8(April 17, 2008)
- ISSN：1523-7052
文摘
We present a mild and efficient method for the completely regioselective alcoholysis of styrene oxides utilizing a cooperative Br
h.gif">nsted acid-type organocatalytic system comprised of mandelic acid (1 mol %) and N,N'-bis-[3,5-bis-(trifluoromethyl)phenyl]-thiourea (1 mol %). Variousstyrene oxides are readily transformed into their corresponding 
hars/beta2.gif" BORDER=0 ALIGN="middle">-alkoxy alcohols in good to excellent yields at full conversion. Simple aliphaticand sterically demanding, as well as unsaturated and acid-sensitive alcohols can be employed.
h.gif">nsted acid-type organocatalytic system comprised of mandelic acid (1 mol %) and N,N'-bis-[3,5-bis-(trifluoromethyl)phenyl]-thiourea (1 mol %). Variousstyrene oxides are readily transformed into their corresponding hars/beta2.gif" BORDER=0 ALIGN="middle">-alkoxy alcohols in good to excellent yields at full conversion. Simple aliphaticand sterically demanding, as well as unsaturated and acid-sensitive alcohols can be employed.