10.1007/BF00948247
The study focuses on the reaction dynamics of α,β-unsaturated aldehydes with acetone cyanohydrin in the presence of diethylamine. It explores how the structure of the reactants influences the reaction's direction, continuing previous investigations. The research demonstrates that aldehydes like crotonaldehyde and 3,3-dimethylacrylaldehyde react with acetone cyanohydrin and diethylamine to form aminonitriles while maintaining their trans configuration. However, acrolein and certain other aldehydes tend to polymerize under the same conditions. The study also observes a shift in the double bond position in the reaction with trans-octatriene-2,4,6-al, leading to the formation of cyanenamine. The products' structures were confirmed through IR, PMR, and mass spectrometry, along with elemental analysis. The study further investigates the reactions at elevated temperatures, leading to the formation of saturated derivatives of cyanamines. The experimental section details the methods used for GLC analysis, PMR and IR spectroscopy, and mass spectrometry, providing a comprehensive approach to understanding the reaction mechanisms and product characterization.
10.1016/S0040-4020(01)92455-X
The research focuses on the reactivity of secondary lithium dialkylcuprates with α,β-ethylenic aldehydes, exploring the formation of 1,2 and 1,4 addition products. The study aims to understand the influence of the cuprate's metal component (magnesium or lithium) and the structure of the aldehydes on the reaction outcomes. The conclusions drawn from the research indicate that secondary alkyl cuprates yield a mixture of 1,2 and 1,4 addition products, while allylic or acetylenic cuprates predominantly yield 1,2 addition products. In contrast, homoallylic, vinylic, and phenyl cuprates exclusively give 1,4 addition products. The research also highlights that chloromagnesium dimethyl cuprate in THF is the most favorable for 1,4 addition. Key chemicals used in the process include various organocuprates and organocopper reagents, such as dialkylcuprates of lithium, methylcopper, and dimethylcuprate of chloromagnesium, as well as α,β-ethylenic aldehydes like acrolein, crotonaldehyde, and methyl-2-pentene-2-al.
10.1021/ol201426c
The research aims to develop an efficient formal synthesis of SCH 351448, a compound that activates the low-density lipoprotein receptor (LDL-R) and has potential for treating hypercholesterolemia. The study utilizes a combination of tandem cross-metathesis (CM)/oxa-Michael reaction, 1,4-syn aldol reaction, tandem oxidation/oxa-Michael reaction, and Suzuki coupling reaction to synthesize the target compound. Key chemicals involved include hydroxy alkene 10, (E)-crotonaldehyde, tetrahydropyran aldehyde 8, ketone 9, epoxide 6, dithiane 7, and alkyne 4. The researchers successfully demonstrated the utility of these tandem reactions under mild conditions, achieving high yields and stereoselectivity. The study concludes that the convergent synthetic route is effective and could be broadly applicable for synthesizing analogues of SCH 351448 for further biological studies.
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