Search

The first water-tolerant, ketone-type indium homoenolate is prepared via the oxidative addition of In/In[Cl.sub.3] to enones, where the reaction has proceeded in aqueous media. The synthetic utility of the indium homoenolate is shown by the synthesis of 1,4-dicarbonyl compounds by palladium-catalyzed coupling of indium homoenolate with acid chloride.

Highly efficient catalytic enantioselective cationic polyene cyclization and catalytic enantioselective intramolecular carbonyl-ene reaction with high enantioselectivities are described. The relationship and mechanistic differences between the two enantioselective reactions are analyzed.

An efficient one-pot synthesis of 4,5,6-triaryl-3,4-dihydropyrimidin-2(1H)-ones through a three-component Biginelli-type condensation of aldehyde, 2-phenylacetophenone, and urea/thiourea in the presence of a catalytic amount of t-BuOK (20 mol %) is described. The reactions proceeded efficiently at 70 degree [Celsius] to produce the desired products in moderate to good yields.

An efficient method is developed for the Barbier-Grignard-type alkylation reaction of aldehydes that uses unactivated alkyl halides in water. A radical type reaction mechanism is studied and proposed by using 4-pentenal as substrate.

An efficient method for the Barbier-type alkylation reaction of various nitrones (including chiral version) and alkyl halides in water is described. The amines and hydroxylamines can be obtained in good yields, depending on the judicious choice of the metal complexes used. [ABSTRACT FROM AUTHOR]

An efficient system of In/CuI/InCl3was developed for Barbier−Grignard-type alkylation reactions of simple imines, using a one-pot condensation of various aldehydes, amines (including aliphatic and chiral version), and alkyl iodides in water or aqueous media. The reactions proceeded efficiently at room temperature to give the desired products in moderate to good yields. Good diastereoselectivities were obtained when using l-valine methyl ester as substrate. [ABSTRACT FROM AUTHOR]