Molecules | |
Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids | |
Yuji Takagi1  Tsunehisa Hirashita1  Shuki Araki1  Takayuki Noda1  Fusako Takahashi1  | |
[1] Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan; | |
关键词: indium; allylation; ionic liquids; carbonyl compounds; homoallylic alcohols; | |
DOI : 10.3390/molecules23071696 | |
来源: DOAJ |
【 摘 要 】
The In-mediated allylation of carbonyl compounds can be performed in various types of solvents including ionic liquids. However, we have found that in [bmim][BF4] (where bmim = 1-butyl-3-methylimidazolium), the In-mediated coupling of crotyl bromide with benzaldehyde gives a complex mixture, and some additives, such as halides and amines, are crucial for the successful conversion to the corresponding γ-adduct. Instead, the addition of alcohols or water promotes the formation of the α-adduct. An asymmetric induction with up to 62% enantiomeric excess (ee) was observed employing cinchonidine as an additive in a binary solvent consisting of an ionic liquid and dichloromethane.
【 授权许可】
Unknown