The development of organometallic-type reactions in aqueous media is reviewed. Coupling reactions of allyl halides with carbonyl compounds mediated by zinc, or tin, or indium in aqueous media to give homoallylic alcohols are discussed. The stereochemical outcome is compared with similar reactions in organic solvents. A concise synthesis of (+)-muscarine is used to illustrate the usefulness of aqueous organometallic-type reactions in organic synthesis. The procedure to protect–deprotect hydroxy functional groups may not be necessary in these reactions. An application in the carbohydrate area is demonstrated with the synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). The mechanistic possibilities of organometallic-type reactions in aqueous media are outlined.

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It was found that ZSM-5 as a green catalyst could efficiently catalyze the reaction of various primary amines with α,β-dicarboxyl compounds to afford β-enaminones in good yields at room temperature. The method provides a novel, simple and convenient route to substitute β-enaminones from primary amines and α,β-dicarboxyl compounds. The catalyst could also be recovered easily.

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