Addition of Enolates and Silyl Enol Ethers of Cycloalkanones to Levoglucosenone in the Presence of Lewis Acids

被引：1
|
作者：
Khahlova, Y. A. [1 ]
Faizullina, L. Kh [1 ]
Valeev, F. A. [1 ]
机构：
[1] Russian Acad Sci, Ufa Res Ctr, Ufa Inst Chem, Pr Oktyabrya 71, Ufa 450054, Republic Of Bas, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 55卷 / 08期
基金：
俄罗斯基础研究基金会;
关键词：
levoglucosenone; cycloalkanones; Michael adducts; 1,2-and 1,4-addition; MICHAEL-ADDITION;
D O I：
10.1134/S1070428019080050
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The addition of lithium enolates and TMS ethers of cyclohexanone and cyclododecanone to levoglucosenone in the presence of Lewis acids was studied. It was established that the optimal way to obtain of Michael adducts involves the reaction levoglucosenone at -78 degrees C with lithium enolates of cyclohexanone and cyclododecanone in the presence of ZnCl2. Additional amounts of Michael adducts can be obtained by treatment of 1,2-adducts with lithium diisopropylamine. 1,2-Adducts are best prepared by the reaction of the corresponding lithium enolates with levoglucosenone in the presence of Ti(Oi-Pr)(4).
引用
收藏
页码：1088 / 1092
页数：5
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