59660-68-3Relevant articles and documents
Development of a Scalable Lanthanide Halide/Quaternary Ammonium Salt System for the Nucleophilic Addition of Grignard Reagents to Carbonyl Groups and Application to the Synthesis of a Remdesivir Intermediate
Brak, Katrien,Bremner, W. Stacy,Brown, Angela M.,Chtchemelinine, Andrei,Heumann, Lars,Kerschen, James A.,Stevens, Andrew C.,Subotkowski, Witold,Vieira, Tiago,Wolfe, Lydia C.,Xu, Boran,Yu, Chia-Yun
, (2021/08/30)
This manuscript describes the development and implementation of a scalable additive system, consisting of a lanthanide salt and a solubilizing quaternary ammonium salt, to improve the yield and robustness of the addition of an organomagnesium reagent to a
Observation of 1,3-diketones formation in the reaction of bulky acyl chlorides with methyllithium
Zhang, Jian,Yang, Nianfa,Yang, Liwen
experimental part, p. 6415 - 6423 (2012/09/08)
The formation of 1,3-diketones was observed in the reactions of bulky acyl chlorides with methyllithium. The reaction products depend on the steric hindrance around the carbonyl group of the acyl chloride and the electronic effect of the group(s) linked to the carbonyl. When the steric hindrance around the carbonyl group of the acyl chloride is big enough, the 1,3-diketone is the only product. In the case of the moderate hindrance around the carbonyl group of the acyl chloride, a moderate yield of 1,3-diketone is obtained and some tertiary alcohol is generated. When there is no steric hindrance around the carbonyl group of the acyl chloride, the tertiary alcohol is the only product. When the steric hindrance around the carbonyl group is moderate and an electron-donating group is connected to the carbonyl of the acyl chloride, all three products-ketone, 1,3-diketone and tertiary alcohol-can be isolated from the reaction mixture after long reaction times.
Soluble lanthanide salts (LnCl3,·2 LiCl) for the improved addition of organomagnesium reagents to carbonyl compounds
Krasovskiy, Arkady,Kopp, Felix,Knochel, Paul
, p. 497 - 500 (2007/10/03)
(Chemical Equation Presented) Easy-to-prepare solutions of LnCl 3·2 LiCl (Ln = La, Ce, Nd) (0.3-0.5 M in THF) are a unique source of soluble lanthanide salts with versatile applications in organic synthesis. These salts can serve as promoters or catalysts for the addition of organometallic compounds to sterically hindered, enolizable or α,β-unsaturated ketones or imines.