Tunable and Diastereoselective Brønsted Acid Catalyzed Synthesis of β-Enaminones
详细信息 查看全文
- 作者：Ye-Won Kang ; Yu Jin Cho ; Seung Jin Han ; Hye-Young Jang
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：January 15, 2016
- 年：2016
- 卷：18
- 期：2
- 页码：272-275
- 全文大小：314K
- ISSN：1523-7052
文摘
The Br?nsted acid catalyzed Meyer–Schuster reaction of hemiaminals was studied for the stereoselective synthesis of β-enaminones. Hemiaminals were formed from propargyl aldehydes (or the oxidation of propargyl alcohols) and amines in the presence of Br?nsted acids. A critical step to control the stereochemistry of the products is the protonation of the corresponding allenol intermediate, which is dictated by the Br?nsted acid used, the steric effect of the amine, and the electronic effect of the propargyl aldehyde.