Tsung-Hsun Chuang

Tin Mediated Allylation Reactions of Enol Ethers in Water

Under tin-mediated Barbier-type reaction conditions, hydration of enol ethers takes place to form aldehydes that undergo allylation reactions. By using this process, various homoallylic alcohols and 2-halohomoallylic alcohols are produced in good to excellent yields.

Nitroalkenes as Carbonyl Surrogates in Arylmethyl-homoallylic Alcohol Forming One-Pot Allylation Reactions in Water

A simple and practical approach has been developed for conducting direct, homoallylic alcohol forming allylation reactions of nitroalkenes in water. Employing the new method, various arylmethyl-homoallylic alcohols can be produced from the corresponding, readily prepared β-nitrostyrenes.

γ-Halo-enones: A Method for their Synthesis from Arylacyl Halides and Their Application to the Preparation of Five-Membered Ring Heterocycles

A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.

SnCl2/TiCl3-Mediated Deoximation of Oximes in an Aqueous Solvent

A simple procedure for SnCl2/TiCl3-mediated deoximation of ketoximes in an aqueous solvent is reported. Under the conditions developed in this effort, various ketones and aldehydes are produced in good to excellent yields.

Methods for the preparation of allenes employing indium- and zinc-mediated dehalogenation reactions in aqueous solutions.

Simple and mild methods for the synthesis of allenes, employing indium- and zinc-mediated dehalogenation reactions of vicinal dihalides in an aqueous solvent, are described. By using these procedures, various allenylmethyl aryl ethers and monosubstituted allenes have been prepared in good to excellent yields.

Hypervalent Iodine(III)-Induced Domino Oxidative Cyclization for the Synthesis of Cyclopenta[b]furans

A new strategy for cyclopenta[b]furan synthesis mediated by hypervalent iodine(III) has been described. The approach employs diacetoxyiodobenzene-induced initial dehydrogenation to a putative trienone intermediate and triggered sequential cycloisomerization to form the cyclo-penta[b]furan targets.