无催化、非对映选择性的烯醇式 Mukaiyama 缩醛反应在水相介质中的研究：吡咯与呋喃 2-硅氧基二烯的比较。
Uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reactions on aqueous media: pyrrole vs furan 2-silyloxy dienes.
机构信息
Dipartimento Farmaceutico, Università degli Studi di Parma, Viale G. P. Usberti 27A, I-43124 Parma, Italy.
出版信息
J Org Chem. 2010 Dec 17;75(24):8681-4. doi: 10.1021/jo101799e. Epub 2010 Nov 18.
PMID:21086960
Abstract
The first uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reaction is reported, between pyrrole/furan-based dienoxy silanes and aromatic aldehydes on salty water/methanol medium, at almost human body temperature, under ultrasonic irradiation. With pyrrole dienes the reaction is anti-selective, while that of furan dienes is syn-selective. The dual role of water as both reaction medium and promoter is highlighted.
摘要
首次报道了在盐/甲醇介质中，在超声辐射下，接近人体温度下，吡咯/呋喃二烯氧基硅烷与芳醛之间的非催化、非对映选择性的Mukaiyama 烯醇缩合反应。对于吡咯二烯，反应是反选择性的，而呋喃二烯则是顺选择性的。突出了水作为反应介质和促进剂的双重作用。
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